Polymerizable liquid crystal composition, optically anisotropic film, optical film, polarizing plate, image display device, and organic electroluminescent display device

ABSTRACT

A polymerizable liquid crystal composition capable of manufacturing an optically anisotropic film having excellent light fastness; and an optically anisotropic film, an optical film, a polarizing plate, an image display device, and an organic electroluminescent display device, each of which uses the polymerizable liquid crystal composition. The polymerizable liquid crystal composition of an embodiment of the present invention contains a polymerizable liquid crystal compound having reverse-wavelength dispersion properties and an aromatic polyether-based compound.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of PCT International Application No.PCT/JP2017/042411 filed on Nov. 27, 2017, which was published under PCTArticle 21(2) in Japanese, and which claims priority under 35 U.S.C. §119(a) to Japanese Patent Application No. 2016-231479 filed on Nov. 29,2016. The above applications are hereby expressly incorporated byreference, in their entirety, into the present application.

BACKGROUND OF THE INVENTION 1. Field of the Invention

The present invention relates to a polymerizable liquid crystalcomposition, an optically anisotropic film, an optical film, apolarizing plate, an image display device, and an organicelectroluminescent display device.

2. Description of the Related Art

A polymerizable compound exhibiting reverse-wavelength dispersionproperties enables, for example, conversion of an accurate light raywavelength over a wide wavelength range and reduction in the thicknessof a retardation film due to a high refractive index, and therefore, thepolymerizable compound has been actively studied.

Furthermore, for the polymerizable compound exhibitingreverse-wavelength dispersion properties, T-type molecular designguidelines have been generally taken, and it has been required todecrease the wavelength of a long molecular axis and increase thewavelength of a short axis positioned in the center of the molecule.

In this regard, it is known that a cycloalkylene skeleton having noabsorption wavelength is used for the connection between a skeleton ofthe short axis positioned in the center of the molecule (hereinafteralso referred to as a “reverse-wavelength dispersion expressingportion”) and the long molecular axis (see, for example, JP2008-273925A,JP2010-031223A, WO2014/010325A, JP2016-081035A, and WO2016/114346A).

SUMMARY OF THE INVENTION

The present inventors have studied a polymerizable liquid crystalcomposition containing the polymerizable compound described inJP2008-273925A, JP2010-031223A, WO2014/010325A, JP2016-081035A, andWO2016/114346A, and have thus found that the light fastness of anoptically anisotropic film thus formed is deteriorated, depending on thetype of the polymerizable compound and the blending conditions ofadditives.

Therefore, the present invention has an object to provide apolymerizable liquid crystal composition capable of manufacturing anoptically anisotropic film having excellent light fastness; and anoptically anisotropic film, an optical film, a polarizing plate, animage display device, and an organic electroluminescent display device,each of which uses the polymerizable liquid crystal composition.

The present inventors have conducted extensive studies on the object,and as a result, they have found that the light fastness of an opticallyanisotropic film thus formed is improved by using a polymerizable liquidcrystal compound exhibiting reverse-wavelength dispersion properties incombination with an aromatic polyether-based compound, therebycompleting the present invention.

That is, the present inventors have found that the object can beaccomplished by the following configurations.

[1] A polymerizable liquid crystal composition comprising:

a polymerizable liquid crystal compound having reverse-wavelengthdispersion properties; and

an aromatic polyether-based compound.

[2] The polymerizable liquid crystal composition as described in [1],

in which the aromatic polyether-based compound includes at least onecompound selected from the group consisting of Formula (A) which will bedescribed later and Formula (B) which will be described later,

in Formula (A) which will be described later, R^(1A) and R^(2A) eachindependently represent a monovalent organic group, R^(3A), R^(4A),R^(5A), and R^(6A) each independently represent a hydrogen atom or amonovalent substituent, and R^(1A) and R^(2A), R^(2A) and R^(3A), R^(3A)and R^(4A), R^(4A) and R^(5A), R^(5A) and R^(6A), or R^(6A) and R^(1A)may be bonded to each other to form a ring, and

in Formula (B) which will be described later, R^(1B) and R^(4B) eachindependently represent a monovalent organic group, R^(2B), R^(3B),R^(5B), and R^(6B) each independently represent a hydrogen atom or amonovalent substituent, and R^(1B) and R^(2B), R^(2B) and R^(3B), R^(3B)and R^(4B), R^(4B) and R^(5B), R^(5B) and R^(6B), or R^(6B) and R^(1B)may be bonded to each other to form a ring.

[3] The polymerizable liquid crystal composition as described in [2],

in which the compound represented by Formula (A) which will be describedlater is a compound represented by Formula (C) which will be describedlater or Formula (D) which will be described later,

in Formula (C) which will be described later, R^(1C), R^(2C), R^(6C),and R^(7C) each independently represent a monovalent organic group,R^(3C), R^(5C), R^(8C) and R^(11C) each independently represent ahydrogen atom or a monovalent substituent, and R^(4C), R^(9C), andR^(10C) each independently represent a hydrogen atom or a monovalentorganic group, and

in Formula (D) which will be described later, R^(1D) represents analkylene group having 1 to 3 carbon atoms, R^(2D), R^(3D), R^(4D), andR^(5D) each independently represent a hydrogen atom or a monovalentsubstituent, and R^(2D) and R^(3D), or R^(3D) and R^(4D) may be bondedto each other to form a ring.

[4] The polymerizable liquid crystal composition as described in [2] or[3],

in which the compound represented by Formula (B) which will be describedlater is a compound represented by Formula (E) which will be describedlater or Formula (F) which will be described later,

in Formula (E) which will be described later, R^(1E), R^(2E), R^(3E),R^(4E), R^(5E), and R^(6E) each independently represent a hydrogen atomor a monovalent organic group, R^(7E), R^(9E), and R^(10E) eachindependently represent a hydrogen atom or a monovalent substituent,R^(8E) represents a monovalent organic group, and R^(1E) and R^(2E), orR^(3E) and R^(4E) may be bonded to each other to form a ring, and

in Formula (F) which will be described later, R^(1F) and R^(4F) eachindependently represent a monovalent organic group, and R^(2F), R^(3F),R^(5F), and R^(6F) each independently represent a hydrogen atom or amonovalent substituent.

[5] The polymerizable liquid crystal composition as described in any oneof [1] to [4],

in which the polymerizable liquid crystal compound which will bedescribed later is a liquid crystal compound represented by Formula (I),L¹-SP¹-A¹-D³-G¹-D¹-Ar-D²-G²-D⁴-A²-SP²-L²  (I)

in Formula (I), D¹, D², D³, and D⁴ each independently represent a singlebond, —CO—O—, —C(═S)O—, —CR¹R²—, —CR¹R²—CR³R⁴—, —O—CR¹R²—,—CR¹R²—O—CR³R⁴—, —CO—O—CR¹R²—, —O—CO—CR¹R²—, —CR¹R²—O—CO—CR³R⁴—,—CR¹R²—CO—O—CR³R⁴—, —NR¹—CR²R³—, or —CO—NR¹—, and R¹, R², R³, and R⁴each independently represent a hydrogen atom, a fluorine atom, or analkyl group having 1 to 4 carbon atoms,

G¹ and G² each independently represent a divalent alicyclic hydrocarbongroup having 5 to 8 carbon atoms, and one or more of —CH₂—'sconstituting the alicyclic hydrocarbon group may be substituted with—O—, —S—, or —NH—,

A¹ and A² each independently represent an aromatic ring having 6 or morecarbon atoms or a cycloalkylene ring having 6 or more carbon atoms,

SP¹ and SP² each independently represent a single bond, a linear orbranched alkylene group having 1 to 12 carbon atoms, or a divalentlinking group in which one or more of —CH₂—'s constituting the linear orbranched alkylene group having 1 to 12 carbon atoms are substituted with—O—, —S—, —NH—, —N(Q)-, or —CO—, and Q represents a substituent,

L¹ and L² each independently represent a monovalent organic group, andat least one of L¹ or L² represents a polymerizable group, provided thatin a case where Ar is an aromatic ring represented by Formula (Ar-3), atleast one of L¹, L², or L³ or L⁴ in Formula (Ar-3) represents apolymerizable group,

Ar represents any one aromatic ring selected from the group consistingof groups represented by Formulae (Ar-1) to (Ar-5) which will bedescribed later,

here, in Formulae (Ar-1) to (Ar-5) which will be described later, *1represents a bonding position with D¹ and *2 represents a bondingposition with D²,

Q¹ represents N or CH,

Q² represents —S—, —O—, or —N(R⁵)—, and R⁵ represents a hydrogen atom oran alkyl group having 1 to 6 carbon atoms,

Y¹ represents an aromatic hydrocarbon group having 6 to 12 carbon atomsor aromatic heterocyclic group having 3 to 12 carbon atoms, which mayhave a substituent,

Z¹, Z², and Z³ each independently represent a hydrogen atom, amonovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, amonovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, amonovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, ahalogen atom, a cyano group, a nitro group, —NR⁶R⁷, or —SR⁸, R⁶ to R⁸each independently represent a hydrogen atom or an alkyl group having 1to 6 carbon atoms, and Z¹ and Z² may be bonded to each other to form anaromatic ring,

A³ and A⁴ each independently represent a group selected from the groupconsisting of —O—, —N(R⁹)—, —S—, and —CO—, and R⁹ represents a hydrogenatom or a substituent,

X represents a hydrogen atom or a non-metal atom of Groups 14 to 16 towhich a substituent may be bonded,

D⁵ and D⁶ each independently represent a single bond, —CO—O—, —C(═S)O—,—CR¹R²—, —CR¹R²—CR³R⁴—, —O—CR¹R²—, —CR¹R²—O—CR³R⁴—, —CO—O—CR¹R²—,—O—CO—CR¹R²—, —CR¹R²—O—CO—CR³R⁴—, —CR¹R²—CO—O—CR³R⁴—, —NR¹—CR²R³—, or—CO—NR¹—, and R¹, R², R³, and R⁴ each independently represent a hydrogenatom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms,

SP³ and SP⁴ each independently represent a single bond, a linear orbranched alkylene group having 1 to 12 carbon atoms, or a divalentlinking group in which one or more of —CH₂—'s constituting the linear orbranched alkylene group having 1 to 12 carbon atoms are substituted with—O—, —S—, —NH—, —N(Q)-, or —CO—, and Q represents a substituent,

L³ and L⁴ each independently represent a monovalent organic group, andat least one of L³, L⁴, or L¹ or L² in Formula (I) represents apolymerizable group,

Ax represents an organic group having 2 to 30 carbon atoms, which has atleast one aromatic ring selected from the group consisting of anaromatic hydrocarbon ring and an aromatic heterocyclic ring,

Ay represents a hydrogen atom, an alkyl group having 1 to 6 carbon atomswhich may have a substituent, or an organic group having 2 to 30 carbonatoms, which has at least one aromatic ring selected from the groupconsisting of an aromatic hydrocarbon ring and an aromatic heterocyclicring,

the aromatic rings in Ax and Ay may have a substituent, and Ax and Aymay be bonded to each other to form a ring, and

Q³ represents a hydrogen atom or an alkyl group having 1 to 6 carbonatoms which may have a substituent.

[6] The polymerizable liquid crystal composition as described in [5],

in which a pKa of a compound used for the formation of Ar in Formula (I)is 5.8 to 10.0.

[7] The polymerizable liquid crystal composition as described in any oneof [1] to [6],

in which a content of the aromatic polyether-based compound is 0.1 to 50parts by mass with respect to 100 parts by mass of the polymerizableliquid crystal compound.

[8] An optically anisotropic film obtained by polymerization of thepolymerizable liquid crystal composition as described in any one of [1]to [7],

[9] An optical film comprising the optically anisotropic film asdescribed in [8],

[10] The optical film as described in [9],

in which the optically anisotropic film is a positive A plate or apositive C plate.

[11] The optical film as described in [9] or [10], comprising two ormore layers of the optically anisotropic films,

in which at least one of the layers is a positive A plate and at leastone of the other layers is a positive C plate.

[12] A polarizing plate comprising:

the optical film as described in any one of [9] to [11]; and

a polarizer.

[13] An image display device comprising the optical film as described inany one of [9] to [11] or the polarizing plate as described in [12],

[14] An organic electroluminescent display device comprising:

an organic electroluminescent display panel; and

a circularly polarizing plate arranged on the organic electroluminescentdisplay panel,

in which the circularly polarizing plate includes a polarizer and theoptical film as described in [11],

According to the present invention, it is possible to provide apolymerizable liquid crystal composition capable of manufacturing anoptically anisotropic film having excellent light fastness; and anoptically anisotropic film, an optical film, a polarizing plate, animage display device, and an organic electroluminescent display device,each of which uses the polymerizable liquid crystal composition.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1A is a schematic cross-sectional view showing an example of anoptical film of an embodiment of the present invention.

FIG. 1B is a schematic cross-sectional view showing an example of anoptical film of the embodiment of the present invention.

FIG. 1C is a schematic cross-sectional view showing an example of anoptical film of the embodiment of the present invention.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, the present invention will be described in detail.

The following description of the constitutional requirements is madebased on representative embodiments of the present invention in somecases, but it should not be construed that the present invention islimited to such embodiments.

Furthermore, in the present specification, a numerical range expressedusing “to” means a range that includes the preceding and succeedingnumerical values of “to” as the lower limit value and the upper limitvalue, respectively.

In the present specification, the bonding direction of a divalent group(for example, —CO—O—) expressed is not particularly limited, and forexample, in a case where D¹ in Formula (I) which will be described lateris —CO—O—, D¹ may be either *1-CO—O—*2 or *1-O—CO—*2, in which *1represents a position bonding to the Ar side and *2 represents aposition bonding to the G¹ side.

[Polymerizable Liquid Crystal Composition]

A polymerizable liquid crystal composition of an embodiment of thepresent invention contains a polymerizable liquid crystal compoundhaving reverse-wavelength dispersion properties (hereinafter simplyreferred to as “reverse dispersion” in some cases) and an aromaticpolyether-based compound.

Using the polymerizable liquid crystal composition of the embodiment ofthe present invention, an optically anisotropic film having excellentlight fastness can be manufactured. Details of a reason therefor arestill not clear, but are presumed to be as follows.

In a case where the optical film is irradiated with light in thepresence of oxygen, electrons are generated from the aromaticpolyether-based compound. Here, an energy level of the highest occupiedmolecular orbital (HOMO) of the aromatic polyether-based compound ishigher than the energy level of the HOMO of the polymerizable liquidcrystal compound. Thus, it is presumed that the electrons generated fromthe aromatic polyether-based compound replace the electrons generatedfrom the polymerizable liquid crystal compound, and they move to thelowest unoccupied molecular orbital (LUMO) of singlet oxygen. As aresult, it is presumed that the decomposition of the polymerizableliquid crystal compound is suppressed, and thus, the light fastness ofthe optically anisotropic film is improved.

Particularly, such the effect is more remarkably exerted by using acompound having a low pKa (preferably a pKa of 10 or more) as a compound(for example, a compound used for formation of Ar in Formula (I)) usedfor the formation of a core portion of the polymerizable liquid crystalcompound. That is, due to a lower pKa of the compound used for theformation of a core portion of the polymerizable liquid crystalcompound, the HOMO of the polymerizable liquid crystal compound islowered. As a result, an energy difference between the singlet oxygenand the LUMO is generated, and thus, the polymerizable liquid crystalcompound itself is light-fastened.

[Polymerizable Liquid Crystal Compound]

The polymerizable liquid crystal composition of the embodiment of thepresent invention contains a polymerizable liquid crystal compoundhaving reverse-wavelength dispersion properties.

Here, in the present specification, the polymerizable liquid crystalcompound having “reverse-wavelength dispersion properties” indicatesthat an in-plane retardation (Re) value becomes equal to or higher withan increase in a measurement wavelength in a case where the in-plane Revalue at a specific wavelength (visible light range) of a retardationfilm manufactured using the polymerizable liquid crystal compound ismeasured.

Furthermore, in the present specification, the “polymerizable liquidcrystal compound” refers to a liquid crystal compound having apolymerizable group. The type of polymerizable group contained in thepolymerizable liquid crystal compound is not particularly limited, andexamples thereof include an acryloyl group, a methacryloyl group, avinyl group, a styryl group, and an allyl group.

The type of the polymerizable liquid crystal compound is notparticularly limited, but can be classified into a rod-like type(rod-like liquid crystal compound) and a disk-like type (disk-likeliquid crystal compound). Further, the polymerizable liquid crystalcompound encompasses a low molecular type and a high molecular type. Theterm “high molecular” generally refers to a compound having a degree ofpolymerization of 100 or more (Polymer Physics-Phase TransitionDynamics, by Masao Doi, page. 2, published by Iwanami Shoten,Publishers, 1992). In the present invention, any type of liquid crystalcompounds can be used. Two or more kinds of rod-like liquid crystalcompounds, two or more kinds of disk-like liquid crystal compounds, or amixture of the rod-like liquid crystal compound and the disk-like liquidcrystal compound may be used.

Among those, the rod-like liquid crystal compound is preferably usedsince it becomes easy to make a retardation film thus formed function asa positive A plate by homogeneously (horizontally) aligning the rod-likeliquid crystal compound.

The polymerizable liquid crystal compound is not particularly limited aslong as it can form a film having reverse-wavelength dispersionproperties as described above, and for example, the compound representedby General Formula (I) described in JP2008-297210A (in particular, thecompound described in paragraph Nos. [0034] to [0039]), the compoundrepresented by General Formula (1) described in JP2010-084032A (inparticular, the compound described in paragraph Nos. [0067] to [0073]),a liquid crystal compound represented by Formula (I) which will bedescribed later, or the like can be used.

In the present invention, from the viewpoint that the polymerizableliquid crystal compound has more excellent reverse-wavelength dispersionproperties, it is preferable that the polymerizable liquid crystalcompound is a liquid crystal compound represented by Formula (I).L¹-SP¹-A¹-D³-G¹-D¹-Ar-D²-G²-D⁴-A²-SP²-L²  (I)

In Formula (I), D¹, D², D³, and D⁴ each independently represent a singlebond, —CO—O—, —C(═S)O—, —CR¹R²—, —CR¹R²—CR³R⁴—, —O—CR¹R²—,—CR¹R²—O—CR³R⁴—, —CO—O—CR²—, —O—CO—CR¹R²—, —CR¹R²—O—CO—CR³R⁴—,—CR*R²—CO—O—CR³R⁴—, —NR¹—CR²R³—, or —CO—NR¹—. R¹, R², R³, and R⁴ eachindependently represent a hydrogen atom, a fluorine atom, or an alkylgroup having 1 to 4 carbon atoms.

Incidentally, in Formula (I), G¹ and G² each independently represent adivalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and oneor more of —CH₂—'s constituting the alicyclic hydrocarbon group may besubstituted with —O—, —S—, or —NH—.

Furthermore, in Formula (I), A¹ and A² each independently represent anaromatic ring having 6 or more carbon atoms, or a cycloalkylene ringhaving 6 or more carbon atoms.

Moreover, in Formula (I), SP¹ and SP² each independently represent asingle bond, a linear or branched alkylene group having 1 to 12 carbonatoms, or a divalent linking group in which one or more of —CH₂—'sconstituting the linear or branched alkylene group having 1 to 12 carbonatoms are substituted with —O—, —S—, —NH—, —N(Q)-, or —CO—, and Qrepresents a substituent.

In addition, in Formula (I), L¹ and L² each independently represent amonovalent organic group, and at least one of L¹ or L² represents apolymerizable group, provided that in a case where Ar is an aromaticring represented by Formula (Ar-3), at least one of L¹, L², or L³ or L⁴in Formula (Ar-3) represents a polymerizable group.

In Formula (I), the divalent alicyclic hydrocarbon group having 5 to 8carbon atoms represented by each of G¹ and G² is preferably a 5- or6-membered ring. Further, the alicyclic hydrocarbon group may besaturated or unsaturated, but is preferably a saturated alicyclichydrocarbon group. With respect to the divalent alicyclic hydrocarbongroup represented by each of G¹ and G², reference can be made to, forexample, the description in paragraph 0078 of JP2012-021068A, thecontents of which are incorporated herein by reference.

In Formula (I), examples of the aromatic ring having 6 or more carbonatoms represented by each of A¹ and A² include aromatic hydrocarbonrings such as a benzene ring, a naphthalene ring, an anthracene ring,and a phenanthroline ring; and aromatic heterocyclic rings such as afuran ring, a pyrrole ring, a thiophene ring, a pyridine ring, athiazole ring, and a benzothiazole ring. Among those, the benzene ring(for example, a 1,4-phenyl group) is preferable.

In addition, in Formula (I), examples of the cycloalkylene ring having 6or more carbon atoms represented by each of A¹ and A² include acyclohexane ring and a cyclohexene ring. Among those, the cyclohexanering (for example, a cyclohexane-1,4-diyl group) is preferable.

in Formula (I), suitable examples of the linear or branched alkylenegroup having 1 to 12 carbon atoms represented by each of SP¹ and SP²include a methylene group, an ethylene group, a propylene group, and abutylene group.

In Formula (I), the polymerizable group represented by at least one ofL¹ or L² is not particularly limited, but is preferably a polymerizablegroup capable of radical polymerization or cationic polymerization.

A generally known radically polymerizable group can be used as theradically polymerizable group, and suitable examples thereof include anacryloyl group and a methacryloyl group. In this case, it is generallyknown that the acryloyl group exhibits a fast polymerization rate, andthus, the acryloyl group is preferable from the viewpoint of improvementof productivity, but the methacryloyl group can also be used as thepolymerizable group of a highly birefringent liquid crystal.

A generally known cationically polymerizable group can be used as thecationically polymerizable group, and specific examples thereof includean alicyclic ether group, a cyclic acetal group, a cyclic lactone group,a cyclic thioether group, a spiroorthoester group, and a vinyloxy group.Among those, the alicyclic ether group or the vinyloxy group ispreferable, and the epoxy group, the oxetanyl group, or the vinyloxygroup is particularly preferable.

Particularly preferred examples of the polymerizable groups include thefollowing ones.

On the other hand, in Formula (I), Ar represents any one aromatic ringselected from the group consisting of groups represented by Formulae(Ar-1) to (Ar-5). Further, in Formulae (Ar-1) to (Ar-5), *1 represents abonding position with D¹ and *2 represents a bonding position with D².

Here, in Formulae (Ar-1), Q¹ represents N or CH, Q² represents —S—, —O—,or —N(R⁵)—, R⁵ represents a hydrogen atom or an alkyl group having 1 to6 carbon atoms, and Y¹ represents an aromatic hydrocarbon group having 6to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12carbon atoms, each of which may have a substituent.

Specific examples of the alkyl group having 1 to 6 carbon atomsrepresented by R⁵ include a methyl group, an ethyl group, a propylgroup, an isopropyl group, an n-butyl group, an isobutyl group, asec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexylgroup.

Examples of the aromatic hydrocarbon group having 6 to 12 carbon atomsrepresented by Y¹ include aryl groups such as a phenyl group, a2,6-diethylphenyl group, and a naphthyl group.

Examples of the aromatic heterocyclic group having 3 to 12 carbon atomsrepresented by Y¹ include heteroaryl groups such as a thienyl group, athiazolyl group, a furyl group, and a pyridyl group.

Furthermore, examples of the substituent which may be contained in Y¹include an alkyl group, an alkoxy group, and a halogen atom.

As the alkyl group, for example, a linear, branched, or cyclic alkylgroup having 1 to 18 carbon atoms is preferable, an alkyl group having 1to 8 carbon atoms (for example, a methyl group, an ethyl group, a propylgroup, an isopropyl group, an n-butyl group, an isobutyl group, asec-butyl group, a tert-butyl group, and a cyclohexyl group) is morepreferable, an alkyl group having 1 to 4 carbon atoms is still morepreferable, and the methyl group or the ethyl group is particularlypreferable.

As the alkoxy group, for example, an alkoxy group having 1 to 18 carbonatoms is preferable, an alkoxy group having 1 to 8 carbon atoms (forexample, a methoxy group, an ethoxy group, an n-butoxy group, and amethoxy ethoxy group) is more preferable, an alkoxy group having 1 to 4carbon atoms is still more preferable, and the methoxy group or theethoxy group is particularly preferable.

Examples of the halogen atom include a fluorine atom, a chlorine atom, abromine atom, and an iodine atom, and among those, the fluorine atom orthe chlorine atom is preferable.

In addition, in Formulae (Ar-1) to (Ar-5), Z¹, Z², and Z³ eachindependently represent a hydrogen atom, a monovalent aliphatichydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclichydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatichydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyanogroup, a nitro group, —NR⁶R⁷, or —SR⁸, R⁶ to R⁸ each independentlyrepresent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,and Z¹ and Z² may be bonded to each other to form an aromatic ring.

As the monovalent aliphatic hydrocarbon group having 1 to 20 carbonatoms, an alkyl group having 1 to 15 carbon atoms is preferable and analkyl group having 1 to 8 carbon atoms is more preferable. Specifically,a methyl group, an ethyl group, an isopropyl group, a tert-pentyl group(1,1-dimethylpropyl group), a tert-butyl group, or a1,1-dimethyl-3,3-dimethyl-butyl group is still more preferable, and themethyl group, the ethyl group, or the tert-butyl group is particularlypreferable.

Examples of the monovalent alicyclic hydrocarbon group having 3 to 20carbon atoms include monocyclic saturated hydrocarbon groups such as acyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, amethylcyclohexyl group, and an ethylcyclohexyl group; monocyclicunsaturated hydrocarbon groups such as a cyclobutenyl group, acyclopentenyl group, a cyclodecenyl group, a cycloheptenyl group, acyclooctenyl group, a cyclodecenyl group, a cyclopentadienyl group, acyclohexadienyl group, a cyclooctadienyl group, and cyclodecadiene; andpolycyclic saturated hydrocarbon groups such as a bicyclo[2.2.1]heptylgroup, a bicyclo[2.2.2]octyl group, a tricyclo[5.2.1.0^(2,6)]decylgroup, a tricyclo[3.3.1.1^(3,7)]decyl group, atetracyclo[6.2.1.1^(3,6).0^(2,7)]dodecyl group, and an adamantyl group.

Specific examples of the monovalent aromatic hydrocarbon group having 6to 20 carbon atoms include a phenyl group, a 2,6-diethylphenyl group, anaphthyl group, and a biphenyl group, and an aryl group having 6 to 12carbon atoms (particularly a phenyl group) is preferable.

Examples of the halogen atom include a fluorine atom, a chlorine atom, abromine atom, and an iodine atom, and among those, the fluorine atom,the chlorine atom, or the bromine atom is preferable.

On the other hand, specific examples of the alkyl group having 1 to 6carbon atoms represented by each of R⁶ and R⁸ include a methyl group, anethyl group, a propyl group, an isopropyl group, an n-butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, and an n-pentylgroup and an n-hexyl group.

In addition, in Formulae (Ar-2) and (Ar-3), A³ and A⁴ each independentlyrepresent a group selected from the group consisting of —O—, —N(R⁹)—,—S—, and —CO—, and R⁹ represents a hydrogen atom or a substituent.

Examples of the substituent represented by R⁹ include the samesubstituents which may be contained in Y¹ in Formula (Ar-1).

Furthermore, in Formula (Ar-2), X represents a hydrogen atom or anon-metal atom of Groups 14 to 16 to which a substituent may be bonded.

Moreover, examples of the non-metal atom of Groups 14 to 16 representedby X include an oxygen atom, a sulfur atom, a nitrogen atom having asubstituent, and a carbon atom having a substituent, and specificexamples of the substituent include an alkyl group, an alkoxy group, analkyl-substituted alkoxy group, a cyclic alkyl group, an aryl group (forexample, a phenyl group and a naphthyl group), a cyano group, an aminogroup, a nitro group, an alkylcarbonyl group, a sulfo group, and ahydroxyl group.

Furthermore, in Formula (Ar-3), D⁵ and D⁶ each independently represent asingle bond, —CO—O—, —C(═S)O—, —CR¹R²—, —CR¹R²—CR³R⁴—, —O—CR¹R²—,—CR¹R²—O—CR³R⁴—, —CO—O—CR¹R²—, —O—CO—CR¹R²—, —CR¹R²—O—CO—CR³R⁴—,—CR¹R²—CO—O—CR³R⁴—, —NR¹—CR²R³—, or —CO—NR¹—. R¹, R², R³, and R⁴ eachindependently represent a hydrogen atom, a fluorine atom, or an alkylgroup having 1 to 4 carbon atoms.

Moreover, in Formula (Ar-3), SP³ and SP⁴ each independently represent asingle bond, a linear or branched alkylene group having 1 to 12 carbonatoms, or a divalent linking group in which one or more of —CH₂—'sconstituting the linear or branched alkylene group having 1 to 12 carbonatoms are substituted with —O—, —S—, —NH—, —N(Q)-, or —CO—, and Qrepresents a substituent. Examples of the substituent include the sameones as those for the substituent which may be contained in Y¹ inFormula (Ar-1).

Furthermore, in Formula (Ar-3), L³ and L⁴ each independently represent amonovalent organic group, and at least one of L³, L⁴, or L¹ or L² inFormula (I) represents a polymerizable group.

Moreover, in Formulae (Ar-4) to (Ar-5), Ax represents an organic grouphaving 2 to 30 carbon atoms, which has at least one aromatic ringselected from the group consisting of an aromatic hydrocarbon ring andan aromatic heterocyclic ring.

Furthermore, in Formulae (Ar-4) to (Ar-5), Ay represents a hydrogenatom, an alkyl group having 1 to 6 carbon atoms which may have asubstituent, or an organic group having 2 to 30 carbon atoms, which hasat least one aromatic ring selected from the group consisting of anaromatic hydrocarbon ring and an aromatic heterocyclic ring.

Here, the aromatic rings in Ax and Ay may have a substituent, and Ax andAy may be bonded to each other to form a ring.

In addition, Q³ represents a hydrogen atom or an alkyl group having 1 to6 carbon atoms which may have a substituent.

Examples of Ax and Ay include ones described in paragraphs [0039] to[0095] of WO2014/010325A.

Incidentally, specific examples of the alkyl group having 1 to 6 carbonatoms represented by Q³ include a methyl group, an ethyl group, a propylgroup, an isopropyl group, an n-butyl group, an isobutyl group, asec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexylgroup. Examples of the substituent include the same ones as thesubstituents which may be contained in Y¹ in Formula (Ar-1).

Preferred examples of the liquid crystal compound represented by Formula(I) are shown below, but are not limited to these liquid crystalcompounds. Further, the 1,4-cyclohexylene groups in the followingformulae are all a trans-1,4-cyclohexylene group.

No Y1 n II-1-1

6 II-1-2

6 II-1-3

6 II-1-4

6 II-1-5

6 II-1-6

11 II-1-7

8 II-1-8

4 II-1-9

6 II-1-10

6 II-1-11

6 II-1-12

6 II-1-13

6 II-1-14

6 II-1-15

6

No X R1 II-2-1

H II-2-2

H II-2-3

H II-2-4

H II-2-5

CH₃ II-2-6

II-2-7 S H

Furthermore, in the formulae, “*” represents a bonding position.

Moreover, a group adjacent to the acryloyloxy group in Formulae II-2-8and II-2-9 represents a propylene group (a group in which a methyl groupis substituted with an ethylene group), and represents a mixture ofposition isomers having different positions of the methyl groups.

No Ax Ay Q2 II-3-1

H H II-3-2

H H II-3-3

H H II-3-4 Ph Ph H II-3-5

H H II-3-6

H H II-3-7

CH₃ H II-3-8

C₄H₉ H II-3-9

C₆H₁₃ H II-3-10

H II-3-11

H II-3-12

CH₂CN H II-3-13

H II-3-14

H II-3-15

CH₂CH₂OH H II-3-16

H H II-3-17

CH₂CF₃ H II-3-18

H CH₃ II-3-19

H II-3-20

H II-3-21

H II-3-22

H II-3-23

H II-3-24

H II-3-25

C₆H₁₃ H

No Ax Ay Q2 II-3-30

H H II-3-31

H H II-3-32

H H II-3-33 Ph Ph H II-3-34

H H II-3-35

H H II-3-36

CH₃ H II-3-37

C₄H₉ H II-3-38

C₆H₁₃ H II-3-39

H II-3-40

H II-3-41

CH₂CN H II-3-42

H II-3-43

H II-3-46

CH₂CH₂OH H II-3-45

H H II-3-46

CH₂CF₃ H II-3-47

H CH₃ II-3-48

H II-3-49

H II-3-50

H II-3-51

H II-3-52

H II-3-53

H II-3-54

C₆H₁₃ H

The pKa of the compound used for formation of Ar in Formula (I) ispreferably 8.0 to 10.0, more preferably 8.1 to 9.5, and still morepreferably 8.2 to 9.0. By adjusting the pKa of the compound used forformation of Ar to be within the range, the compatibility between thepolymerizable liquid crystal compound and the aromatic polyether-basedcompound is improved. Thus, the durability and the light fastness of theoptically anisotropic film are further improved.

In the present invention, the pKa of the compound used for formation ofAr refers to a first acid dissociation constant (pKa1). The Ar portionin Formula (I) is also referred to as a core portion of thepolymerizable liquid crystal compound, and in a case where the pKa ofthe compound used for formation of the core portion is in a range of 5.8to 10.0, the polymerizable liquid crystal compound havingreverse-wavelength dispersion properties is easily obtained.

Here, the pKa means a pKa in an aqueous solution and is described in,for example, in Chemical Handbook (II) (Revised 4^(th) Edition, 1993,compiled by the Chemical Society of Japan, Maruzen Company, Ltd.), and alower value thereof indicates higher acid strength. Specifically, thepKa in an aqueous solution can be calculated by measuring the aciddissociation constant at 25° C., using an infinite-dilution aqueoussolution, or a value based on Hammett substituent constants and thedatabase of well-known literature can also be determined by computationusing the following software package 1. All the values of pKa describedin the present specification indicate values (pKa calculated) determinedby computation using this software package.

<Software Package 1>

Advanced Chemistry Development (ACD/Labs) Software V 8.14 for Solaris(1994-2007 ACD/Labs).

Specific examples of the compound used for formation of Ar in Formula(I) include the following compounds including phenol structures.

Structure

pKa 8.3 8.42 Structure

pKa 8.71 8.75 Structure

pKa 8.22 8.56 Structure

pKa 7.81 8.66 Structure

pKa 8.72 9 Structure

pKa 7.88 5.88 Structure

pKa 8.41 8.53 Structure

pKa 8.57 8.49 Structure

pKa 8.5 8.45 Structure

pKa 8.85 8.4 Structure

pKa 8.41 Structure

pKa 8.41 8.4 Structure

pKa 8.51 7.84 Structure

pKa 8.71 8.7 Structure

pKa 8.66 8.26 Structure

pKa 8.83

Structure

pKa 8.69 Structure

pKa 8.47 Structure

pKa 8.48 8.67 Structure

pKa 8.79 8.99 Structure

pKa 8.79 8.19 Structure

pKa 8.78 8.48 Structure

pKa 8.57 8.33 Structure

pKa 8.49 8.44 Structure

pKa 8.51 8.53 Structure

pKa 8.83 8.76 Structure

pKa 8.24 8.64 Structure

Pka 9.56 8.82

The polymerizable liquid crystal composition of the embodiment of thepresent invention may contain a liquid crystalline compound havingforward wavelength dispersion properties (hereinafter also referred toas “forward dispersion”), in addition to the above-mentionedpolymerizable liquid crystal compound having reverse-wavelengthdispersion properties.

Here, in the present specification, the liquid crystalline compoundhaving “forward wavelength dispersion properties” refers to a compoundin which an in-plane retardation (Re) value decreases with an increasein a measurement wavelength as the Re value at a specific wavelength(visible light range) of a retardation film manufactured using theliquid crystalline compound is measured.

In the present invention, in a case where the liquid crystallinecompound exhibiting forward wavelength dispersion properties iscontained, the content thereof is not particularly limited, but ispreferably 1 to 40 parts by mass, and more preferably 10 to 30 parts bymass, with respect to 100 parts by mass of a total amount of theabove-mentioned polymerizable liquid crystal compound havingreverse-wavelength dispersion properties and the liquid crystallinecompound exhibiting forward wavelength dispersion properties.

[Aromatic Polyether-Based Compound]

In the present invention, the aromatic polyether-based compound means acompound having a skeleton in which two or more hydrogen atoms in onearomatic ring are substituted with etheric oxygen atoms. Examples of thearomatic ring include a benzene ring and an aromatic heterocyclic ring(for example, a thiophene ring and a pyrrole ring).

The aromatic polyether-based compound may have a plurality of aromaticrings in one molecule. In this case, two or more hydrogen atoms in eachof the plurality of aromatic rings may be substituted with ethericoxygen atoms.

From the viewpoint that the light fastness of the optically anisotropicfilm is further improved, the aromatic polyether-based compoundpreferably includes at least one compound selected from the groupconsisting of Formula (A) and Formula (B) which will be described later.

<Compound Represented by Formula (A)>

First, the compound represented by Formula (A) will be described.

In Formula (A), R^(1A) and R^(2A) each independently represent amonovalent organic group, and R^(3A), R^(4A), R^(5A), and R^(6A) eachindependently represent a hydrogen atom or a monovalent substituent.R^(1A) and R^(2A), R^(2A) and R^(3A), R^(3A) and R^(4A), R^(4A) andR^(5A), R^(5A) and R^(6A), or R^(6A) and R^(1A) may be bonded to eachother to form a ring.

Furthermore, the oxygen atom bonded to each of R^(1A) and R^(2A) shownin Formula (A) represents an etheric oxygen atom.

The monovalent organic group represented by each of R^(1A) and R^(2A)may be an alkyl group (which may be linear, branched, or cyclic, andpreferably has 1 to 20 carbon atoms), an alkenyl group (preferablyhaving 1 to 20 carbon atoms), an aryl group (which may be a monocycle ora fused ring and preferably has 6 to 20 carbon atoms), a heterocyclicgroup (for example, a tetrahydropyranyl group and a pyrimidyl group),—Si(R^(7A))₃ (R^(7A)'s each independently represent a hydrogen atom oran alkyl group, provided that at least one R^(7A)'s is an alkyl group),a monovalent group formed by removing one hydrogen atom from thecompound represented by Formula (A), a monovalent group formed byremoving one hydrogen atom from the compound represented by Formula (B),and a group formed by combination of these groups.

In addition, the monovalent organic group represented by each of R^(1A)and R^(2A) may include —O—, provided that —O— is not directly bonded tothe etheric oxygen atom shown in Formula (A).

The monovalent organic group represented by each of R^(1A) and R^(2A)may have a substituent such as a group represented by (R^(8A))₂NC(═O)—,urea (R^(8A)—NHC(═O)NH—), and a hydroxy group. R^(8A)'s eachindependently represent a hydrogen atom, an aryl group, or an alkylgroup. In a case where R^(8A) is an aryl group or an alkyl group, thegroup may further have a substituent.

Examples of the monovalent substituent in each of R^(3A), R^(4A),R^(5A), and R^(6A) include a halogen atom, an alkyl group (which may belinear, branched, or cyclic, and preferably has 1 to 20 carbon atoms),an alkenyl group (preferably having 1 to 20 carbon atoms), an aryl group(which may be a monocycle or a fused ring, and preferably has 6 to 20carbon atoms), a heterocyclic group (for example, a tetrahydropyranylgroup and a pyrimidyl group), a group represented by (R^(9A))₂NC(═O)—,urea (R^(9A)—NHC(═O)NH—), a monovalent group formed by removing onehydrogen atom from the compound represented by Formula (A), a monovalentgroup formed by removing one hydrogen atom from the compound representedby Formula (B), and a group formed by combination of two or more ofthese groups. R^(9A)'s each independently represent a hydrogen atom, analkyl group, or an aryl group. Further, the alkyl group or the arylgroup in R^(9A) may have a substituent represented byR^(10A)SO₂-(R^(10A) represents an alkyl group).

In a case where R^(3A), R^(4A), R^(5A), or R^(6A) is an alkyl group, analkenyl group, an aryl group, a monovalent group formed by removing onehydrogen atom from the compound represented by Formula (A), or amonovalent group formed by removing one hydrogen atom from the compoundrepresented by Formula (B), the group may include a bond represented by—O—.

In a case where R^(1A) and R^(2A) are bonded to each other to form aring (hetero ring), the number of carbon atoms constituting the ring ispreferably 3 to 5. The ring thus formed may have a substituent such asan alkyl group.

In a case where R^(2A) and R^(3A), or R^(6A) and R^(1A) are bonded toeach other to form a ring (hetero ring), the number of carbon atomsconstituting the ring is preferably 4 to 6. The ring thus formed mayhave a substituent such as an alkyl group.

In a case where R^(3A) and R^(4A), R^(4A) and R^(5A), or R^(5A) andR^(6A) are bonded to each other to form a ring (hydrocarbon ring orhetero ring), the number of carbon atoms constituting the ring ispreferably 5 to 7. The ring thus formed may have a substituent such asan alkyl group and an alkoxy group. Further, the substituents of thering formed may further be bonded to each other to form a ring, and inthis case, a ring formed by the bonding of R^(3A) and R^(4A), R^(4A) andR^(5A), or R^(5A) and R^(6A) and a ring formed by the mutual bonding ofthe substituents may constitute a spiro ring or a fused ring.

An example of suitable aspects of the compound represented by Formula(A) may be a compound represented by Formula (C) or Formula (D).

(Compound Represented by Formula (C))

The compound represented by Formula (C) will be described.

In Formula (C), R^(1C), R^(2C), R^(6C), and R^(7C) each independentlyrepresent a monovalent organic group, R^(3C), R^(5C), R^(8C), andR^(11C) each independently represent a hydrogen atom or a monovalentsubstituent, an R^(4C), R^(9C) and R^(10C) each independently representa hydrogen atom or a monovalent organic group.

Furthermore, the oxygen atom bonded to each of R^(1C), R^(2C), R^(6C),and R^(7C) shown in Formula (C) represents an etheric oxygen atom.

Specific examples of the monovalent organic group represented by each ofR^(1C), R^(2C), R^(6C), and R^(7C) are the same as those of themonovalent organic group represented by each of R^(1A) and R^(2A).

Specific examples of the monovalent substituent represented by each ofR^(3C), R^(5C), R^(8C), and R^(11C) are the same as those of themonovalent substituent represented by each of R^(3A), R^(4A), R^(5A),and R^(6A).

Examples of the monovalent organic group represented by each of R^(4C),R^(9C), and R^(10C) include an alkyl group (which may be linear,branched, or cyclic, and preferably has 1 to 20 carbon atoms), analkenyl group (preferably having 1 to 20 carbon atoms), and an arylgroup (which may be a monocycle or a fused ring, and preferably has 6 to20 carbon atoms), and these groups may have a substituent such as ahalogen atom and an alkoxy group.

(Compound Represented by Formula (D))

The compound represented by Formula (D) will be described.

In Formula (D), R^(1D) represents an alkylene group having 1 to 3 carbonatoms, and R^(2D), R^(3D), R^(4D), and R^(5D) each independentlyrepresent a hydrogen atom or a monovalent substituent. Further, R^(2D)and R^(3D), or R^(3D) and R^(4D) may be bonded to each other to form aring.

Furthermore, the oxygen atom bonded to R^(1D) shown in Formula (D)represents an etheric oxygen atom.

The alkylene group having 1 to 3 carbon atoms represented by R^(1D) maybe substituted with at least one substituent selected from the groupconsisting of a halogen atom, an alkyl group (which may be linear,branched, or cyclic, and preferably has 1 to 20 carbon atoms), an arylgroup (which may be a monocycle or a fused ring, and preferably has 6 to20 carbon atoms), an alkoxy group, an aryloxy group, a group representedby ═S, and a group represented by ═O. Specific examples of thesubstituent in R^(1D) are the same as the substituents of Z in GeneralFormula (I) in JP1987-010420B (JP-S62-010420B).

R^(1D) is preferably an unsubstituted alkylene group, or an alkylenegroup substituted with an alkyl group or an aryl group.

Examples of the monovalent substituent represented by each of R^(2D),R^(3D), R^(4D), and R^(5D) include a halogen atom, an alkyl group, anaryl group (which may be a monocycle or a fused ring), an alkoxy group,an aryloxy group, an alkylthio group, an acyl group, an acylamino group,a sulfonamido group, a diacylamino group, a carboxy group, a sulfogroup, and a hydroxy group, and these substituents may be furthersubstituted. Specific examples of each group are the same as those ofR¹, R², R³, and R⁴ in General Formula (I) in JP1987-010420B(JP-S62-010420B), respectively.

As R^(2D), R^(3D), R^(4D), and R^(5D), a hydrogen atom, a halogen atom,an alkyl group, an alkoxy group, or an alkylthio group is preferable.

In a case where R^(2D) and R^(3D), or R^(3D) and R^(4D) are bonded toeach other to form a ring, examples of the ring include a hydrocarbonring and a hetero ring.

Examples of the hydrocarbon ring that can be formed by the bonding ofR^(2D) and R^(3D), or R^(3D) and R^(4D) include an indane ring, aspiroindane ring, a naphthalene ring, and a tetrahydronaphthalene ring.These hydrocarbon rings may be substituted with a group exemplified as asubstituent of the hydrocarbon ring formed by ring closure of R¹ and R²,or R² and R³ in General Formula (I) in JP1987-010420B (JP-S62-010420B).

Examples of the hetero ring that can be formed by the bonding of R^(2D)and R^(3D), or R^(3D) and R^(4D) include a chroman ring, a coumaranring, a spirochroman ring, and a spirocoumaran ring. These hetero ringsmay be substituted with a group exemplified as a substituent of thehetero ring formed by ring closure of R¹ and R², or R² and R³ in GeneralFormula (I) in JP1987-010420B (JP-S62-010420B).

Out of R^(2D) and R^(3D), and R^(3D) and R^(4D), R^(3D) and R^(4D) arepreferably bonded to each other to form a ring.

The compound represented by Formula (D) may be a compound having askeleton represented by Formula (D-1). The compound having a skeletonrepresented by Formula (D-1) comprises a structure in which R^(3D) andR^(4D) in Formula (D) are bonded to each other to form a spiroindanering, and the spiroindane ring is substituted with a compoundrepresented by Formula (d1).

The definition of R^(6D) in Formula (d1) and Formula (D-1) is the sameas that of R^(1D) in Formula (D), and R^(1D) in Formula (D-1) representsR^(1D) in Formula (D).

The compound represented by Formula (D) may be a compound having askeleton represented by Formula (D-2) or a compound having a skeletonrepresented by Formula (D-3).

The compound having a skeleton represented by Formula (D-2) comprises astructure in which R^(3D) and R^(4D) in Formula (D) are bonded to eachother to form a spirochroman ring, and the spirochroman ring issubstituted with the compound represented by Formula (d1).

The compound having a skeleton represented by Formula (D-3) comprises astructure in which R^(3D) and R^(4D) in Formula (D) are bonded to eachother to form a spirocoumaran ring, and the spirocoumaran ring issubstituted with the compound represented by Formula (d1).

The definition of R^(6D) in Formula (D-2) and Formula (D-3) is the sameas that of R^(1D) in Formula (D), and R^(1D) in Formula (D-2) andFormula (D-3) represents R^(1D) in Formula (D).

Specific examples of the compounds represented by Formula (A), Formula(C), and Formula (D) are shown below.

<Compound Represented by Formula (B)>

Next, the compound represented by Formula (B) will be described.

In Formula (B), R^(1B) and R^(4B) each independently represent amonovalent organic group, and R^(2B), R^(3B), R^(5B), and R^(6B) eachindependently represent a hydrogen atom or a monovalent substituent.R^(1B) and R^(2B), R^(2B) and R^(3B), R^(3B) and R^(4B), R^(4B) andR^(5B), R^(5B) and R^(6B), or R^(6B) and R^(1B) may be bonded to eachother to form a ring.

Furthermore, the oxygen atom bonded to each of R^(1B) and R^(4B) shownin Formula (B) represents an etheric oxygen atom.

Specific examples of the monovalent organic group represented by each ofR^(1B) and R^(4B) are the same as those of the monovalent organic grouprepresented by each of R^(1A) and R^(2A).

Specific examples of the monovalent substituent represented by each ofR^(2B), R^(3B), R^(5B), and R^(6B) are the same as those of themonovalent substituent represented by each of R^(3A), R^(4A), R^(5A),and R^(6A).

In a case where R^(1B) and R^(2B), R^(3B) and R^(4B), R^(4B) and R^(5B),or R^(6B) and R^(1B) are bonded to each other to form a ring (heteroring), the number of carbon atoms constituting the ring is preferably 4to 6. The ring thus formed may have a substituent such as an alkyl groupand an alkoxy group. Further, the substituents of the ring formed mayfurther be bonded to each other to form a ring, and in this case, a ringformed by the bonding of R^(1B) and R^(2B), R^(3B) and R^(4B), R^(4B)and R^(5B), or R^(6B) and R^(1B) and a ring formed by the mutual bondingof the substituents may constitute a spiro ring or a fused ring.

In a case where R^(2B) and R^(3B), or R^(5B) and R^(6B) are bonded toeach other to form a ring (a hydrocarbon ring or a hetero ring), thenumber of carbon atoms constituting the ring is preferably 5 to 7.Further, the ring thus formed may have a substituent such as an alkylgroup.

An example of suitable aspects of the compound represented by Formula(B) may be a compound represented by Formula (E) or Formula (F).

(Compound Represented by Formula (E))

The compound represented by Formula (E) will be described.

In Formula (E), R^(1E), R^(2E), R^(3E), R^(4E), R^(5E), and R^(6E) eachindependently represent a hydrogen atom or a monovalent organic group,R^(7E), R^(9E), and R^(10E) each independently represent a hydrogen atomor a monovalent substituent, and R^(8E) represents a monovalent organicgroup. R^(1E) and R^(2E), or R^(3E) and R^(4E) may be bonded to eachother to form a ring.

Furthermore, the oxygen atom bonded to the benzene ring shown in Formula(E) represents an etheric oxygen atom.

The monovalent organic group represented by each of R^(1E), R^(2E),R^(3E), R^(4E), R^(5E), and R^(6E) may be an alkyl group (which may belinear, branched, or cyclic, and preferably has 1 to 20 carbon atoms),an alkenyl group (preferably having 1 to 20 carbon atoms), an alkoxygroup (which may be linear, branched, or cyclic, and preferably has 1 to20 carbon atoms), an aryl group (which may be a monocycle or a fusedring, and preferably has 6 to 20 carbon atoms), and a group formed bycombination of these groups, and these groups may have a substituentsuch as a halogen atom.

Specific examples of the monovalent substituent represented by each ofR^(7E), R^(9E), and R^(10E) are the same as those of the monovalentsubstituent represented by each of R^(3A), R^(4A), R^(5A), and R^(6A).

The monovalent organic group represented by R^(8E) is the same as themonovalent organic group represented by R^(1A) and R^(2A).

In a case where R^(1E) and R^(2E), or R^(3E) and R^(4E) are bonded toeach other to form a ring (a hydrocarbon ring or a hetero ring), thenumber of carbon atoms constituting the ring is preferably 4 to 6. Thering thus formed may have a substituent such as an alkyl group and analkoxy group. Further, the substituents of the ring formed may furtherbe bonded to each other to form a ring, and in this case, a ring formedby the bonding of R^(1E) and R^(2E), or R^(3E) and R^(4E) and a ringformed by the mutual bonding of the substituents may constitute a fusedring.

Examples of the compound represented by Formula (E), in which R^(1E) andR^(2E) are bonded to each other to form a ring, include a compoundhaving a skeleton represented by Formula (E-1).

The compound having a skeleton represented by Formula (E-1) is acompound having a spirochroman ring structure. R^(8E) in Formula (E-1)represents R^(8E) in Formula (E).

(Compound Represented by Formula (F))

The compound represented by Formula (F) will be described.

In Formula (F), R^(1F) and R^(4F) each independently represent amonovalent organic group, and R^(2F), R^(3F), R^(5F), and R^(6F) eachindependently represent a hydrogen atom or a monovalent substituent.

The monovalent organic group represented by each of R^(1F) and R^(4F) isthe same as the monovalent organic group represented by each of R^(1A)and R^(2A).

The monovalent substituent represented by each of R^(2F), R^(3F),R^(5F), and R^(6F) is the same as the monovalent substituent representedby each of R^(3A), R^(4A), R^(5A), and R^(6A).

Specific examples of the compound represented by each of Formulae (B),(E), and (F) are shown below.

The content of the aromatic polyether-based compound is preferably 0.1to 50 parts by mass, more preferably 0.5 to 30 parts by mass, still morepreferably 1 to 20 parts by mass, and particularly preferably 5 to 20parts by mass, with respect to 100 parts by mass of the polymerizableliquid crystal compound included in the polymerizable liquid crystalcomposition of the embodiment of the present invention. By adjusting thecontent of the aromatic polyether-based compound to be within the range,the light fastness of the optically anisotropic film is furtherimproved.

The aromatic polyether-based compounds may be used alone or incombination of two or more kinds thereof. In a case where two or morekinds of the aromatic polyether-based compounds are used in combination,the total amount thereof is preferably within the range.

[Polymerization Initiator]

The polymerizable liquid crystal composition of the embodiment of thepresent invention preferably contains a polymerization initiator.

The polymerization initiator to be used is preferably aphotopolymerization initiator capable of initiating a polymerizationreaction upon irradiation with ultraviolet rays.

Examples of the photopolymerization initiator include α-carbonylcompounds (described in each of the specifications of U.S. Pat. Nos.2,367,661A and 2,367,670A), acyloin ethers (described in thespecification of U.S. Pat. No. 2,448,828A), α-hydrocarbon-substitutedaromatic acyloin compounds (described in the specification of U.S. Pat.No. 2,722,512A), multinuclear quinone compounds (as described in each ofthe specifications of U.S. Pat. Nos. 3,046,127A and 2,951,758A),combinations of triarylimidazole dimer and p-aminophenyl ketone (asdescribed in the specification of U.S. Pat. No. 3,549,367A), acridineand phenazine compounds (described in each of the specifications ofJP1985-105667A (JP-S60-105667A) and U.S. Pat. No. 4,239,850A),oxadiazole compounds (described in the specification of U.S. Pat. No.4,212,970A), and acyl phosphine oxide compounds (described in each ofthe specifications of JP1988-040799B (JP-S63-040799B), JP1993-029234B(JP-H05-029234B), JP1998-095788A (JP-H10-095788A), and JP1998-029997A(JP-H10-029997A)).

Specific examples of the photopolymerization initiator include Irgacureseries (for example, Irgacure 651, Irgacure 754, Irgacure 184, Irgacure2959, Irgacure 907, Irgacure 369, Irgacure 379, Irgacure 819, andIrgacure OXE-01), available from BASF, Darocure series (for example,Darocure TPO and Darocure 1173), Quantacure PDO, and Ezacure series (forexample, Ezacure TZM, Ezacure TZT, and Ezacure KTO46) available fromLamberti.

In a case where the polymerization initiator is contained, the contentof the polymerization initiator is preferably 0.5 to 10 parts by mass,and more preferably 1 to 10 parts by mass, with respect to 100 parts bymass of the polymerizable liquid crystal compound included in thepolymerizable liquid crystal composition of the embodiment of thepresent invention.

The polymerization initiators may be used alone or in combination of twoor more kinds thereof. In a case where two or more kinds of thepolymerization initiators are used in combination, the total amountthereof is preferably within the range.

[Solvent]

The polymerizable liquid crystal composition of the embodiment of thepresent invention preferably contains a solvent from the viewpoint ofworkability for forming an optically anisotropic film, and the like.

Specific examples of the solvent include ketones (for example, acetone,2-butanone, methyl isobutyl ketone, and cyclohexanone), ethers (forexample, dioxane and tetrahydrofuran), aliphatic hydrocarbons (forexample, hexane), alicyclic hydrocarbons (for example, cyclohexane),aromatic hydrocarbons (for example, toluene, xylene, andtrimethylbenzene), halogenated carbons (for example, dichloromethane,dichloroethane, dichlorobenzene, and chlorotoluene), esters (forexample, methyl acetate, ethyl acetate, and butyl acetate), water,alcohols (for example, ethanol, isopropanol, butanol, and cyclohexanol),cellosolves (for example, methyl cellosolve and ethyl cellosolve),cellosolve acetates, sulfoxides (for example, dimethyl sulfoxide), andamides (for example, dimethylformamide and dimethylacetamide), and thesemay be used alone or in combination of two or more kinds thereof.

[Other Components]

The polymerizable liquid crystal composition of the embodiment of thepresent invention may contain other components than the abovecomponents, and examples of such other components include an antioxidant(for example, a phenol-based antioxidant), a liquid crystal compoundother than the above liquid crystal compounds, an air interfacealignment agent (leveling agent), a surfactants, a tilt angle controlagent, an alignment aid, a plasticizer, and a crosslinking agent.

[Optically Anisotropic Film]

An optically anisotropic film of an embodiment of the present inventionis an optically anisotropic film obtained by polymerization of thepolymerizable liquid crystal composition.

In the present invention, examples of the method for forming theoptically anisotropic film include a method in which the polymerizableliquid crystal composition containing the polymerizable liquid crystalcompound, the aromatic polyether-based compound, the polymerizationinitiator, the solvent, and the like as described above is used to forma desired alignment state and then fixed by polymerization.

Here, the polymerization condition is not particularly limited, but inthe polymerization by irradiation with light, ultraviolet rays arepreferably used. The irradiation dose is preferably 10 mJ/cm² to 50J/cm², more preferably 20 mJ/cm² to 5 J/cm², still more preferably 30mJ/cm² to 3 J/cm², and particularly preferably 50 to 1,000 mJ/cm². Inaddition, the polymerization may be carried out under a heatingcondition in order to accelerate the polymerization reaction.

Moreover, in the present invention, the optically anisotropic film canbe formed on an optional support in the optical film of an embodiment ofthe present invention which will be described later or a polarizer in apolarizing plate of an embodiment of the present invention which will bedescribed later.

[Optical Film]

The optical film of the embodiment of the present invention is anoptical film having the optically anisotropic film of the embodiment ofthe present invention.

FIG. 1A, FIG. 1B, and FIG. 1C (these drawings are hereinafter simplyabbreviated as “FIG. 1” unless it is necessary that they areparticularly distinguished from each other) are each a cross-sectionalview schematically showing an example of the optical film of theembodiment of the present invention.

Furthermore, FIG. 1 is a schematic view, and the thicknessesrelationship, the positional relationship, and the like among therespective layers do not necessarily coincide with actual ones. Any ofthe support, the alignment film and the hard coat layer shown in FIG. 1are both an optional constitutional member.

An optical film 10 shown in FIG. 1 has a support 16, an alignment film14, and an optically anisotropic film 12 in this order.

In addition, the optical film 10 may have a hard coat layer 18 on theside of the support 16 opposite to the side on which the alignment film14 is provided as shown in FIG. 1B, and may have the hard coat layer 18on the side of the optically anisotropic film 12 opposite to the side onwhich the alignment film 14 is provided as shown in FIG. 1C.

Hereinafter, various members used for the optical film of the embodimentof the present invention will be described in detail.

[Optically Anisotropic Film]

The optically anisotropic film contained in the optical film of theembodiment of the present invention is the above-mentioned opticallyanisotropic film of the embodiment of the present invention.

In the optical film of the embodiment of the present invention, thethickness of the optically anisotropic film is not particularly limited,but is preferably 0.1 to 10 μm, and more preferably 0.5 to 5 μm.

In the optical film of the embodiment of the present invention, it ispreferable that the above-mentioned optically anisotropic film of theembodiment of the present invention is a positive A plate or a positiveC plate from the viewpoint of optical designs.

Here, the A plate encompasses two kinds of plates, that is, a positive Aplate and a negative A plate, and in a case where a refractive index inthe slow axis direction in the film plane (a direction in which therefractive index becomes a maximum in the plane) is represented by nx, arefractive index in the direction in-plane orthogonal to the in-planeslow axis is represented by ny, and a refractive index in the thicknessdirection is represented by nz, the positive A plate satisfies therelationship of Formula (A1) and the negative A plate satisfies therelationship of Formula (A2). In addition, in the positive A plate, Rthrepresents a positive value, and in the negative A plate, Rth representsa negative value.nx>ny≈nz  Formula (A1)ny<nx≈nz  Formula (A2)

Furthermore, “≈” encompasses a case where the both are completely thesame as well as a case where the both are substantially the same. Theexpression, “substantially the same” has the following meanings: forexample, a case where (ny−nz)×d (in which d is the thickness of a film)is −10 to 10 nm, and preferably −5 to 5 nm is also included “ny≈nz”, anda case where (nx−nz)×d is −10 to 10 nm, and preferably −5 to 5 nm isalso included in “nx≈nz”.

In addition, the C plate encompasses two kinds of plates, that is, apositive C plate and a negative C plate, the positive C plate satisfiesthe relationship of Formula (C1), and the negative C plate satisfies therelationship of Formula (C2). In addition, in the positive C plate, Rthrepresents a negative value, and in the negative C plate, Rth representsa positive value.nz>nx≈ny  Formula (C1)nz<nx≈ny  Formula (C2)

Furthermore, “≈” encompasses a case where the both are completely thesame as well as a case where the both are substantially the same. Theexpression, “substantially the same” has the following meanings: forexample, a case where (nx−ny)×d (in which d is the thickness of a film)is 0 to 10 nm, and preferably 0 to 5 nm is also included “nx≈ny”.

From the viewpoint of optical designs, it is preferable that the opticalfilm of the embodiment of the present invention is an optical filmhaving the above-mentioned two or more layers of the opticallyanisotropic films of the embodiment of the present invention, in whichat least one of the layers is a positive A plate and at least one of theother layers is a positive C plate.

[Support]

The optical film of the embodiment of the present invention may have asupport as a base material for forming an optically anisotropic film asdescribed above.

Such a support is preferably transparent, and specifically, the supportpreferably has a light transmittance of 80% or more.

Examples of such a support include a glass substrate and a polymer film.Examples of the material for the polymer film include cellulose-basedpolymers; acrylic polymers having acrylic acid ester polymers such aspolymethyl methacrylate and a lactone ring-containing polymer;thermoplastic norbornene-based polymers; polycarbonate-based polymers;polyester-based polymers such as polyethylene terephthalate andpolyethylene naphthalate; styrene-based polymers such as polystyrene andan acrylonitrile-styrene copolymer (AS resin); polyolefin-based polymerssuch as polyethylene, polypropylene, and an ethylene-propylenecopolymer; vinyl chloride-based polymers; amide-based polymers such asnylon and aromatic polyamide; imide-based polymers; sulfone-basedpolymers; polyether sulfone-based polymers; polyether ether ketone-basedpolymers; polyphenylene sulfide-based polymers; vinylidenechloride-based polymers; vinyl alcohol-based polymers; vinylbutyral-based polymers; arylate-based polymers; polyoxymethylene-basedpolymers; epoxy-based polymers; and polymers containing a mixture ofthese polymers.

In addition, in an aspect, the polarizer which will be described latermay also function as such a support.

In the present invention, the thickness of the support is notparticularly limited, but is preferably 5 to 60 μm, and more preferably5 to 30 μm.

[Alignment Film]

In a case where the optical film of the embodiment of the presentinvention has the above-mentioned optional support, it is preferablethat the optical film has an alignment film between the support and theoptically anisotropic film. Further, in an aspect, the above-mentionedsupport may also function as an alignment film.

The alignment film generally has a polymer as a main component. Thematerials for the polymer material for an alignment film are describedin many documents, and many commercially available products can be used.

The polymer material used in the present invention is preferably apolyvinyl alcohol or a polyimide, or a derivative thereof. Particularly,a modified or non-modified polyvinyl alcohol is preferable.

Examples of the alignment film that can be used in the present inventioninclude the alignment films described in Line 24 on Page 43 to Line 8 onPage 49 of WO01/088574A; the modified polyvinyl alcohols described inparagraphs [0071] to [0095] of JP3907735B; and the liquid crystalalignment film formed by a liquid crystal aligning agent described inJP2012-155308A.

In the present invention, for a reason that deterioration in the surfacestate can be prevented by avoiding a contact with the surface of thealignment film upon formation of the alignment film, an opticalalignment film is also preferably used as the alignment film.

The optical alignment film is not particularly limited, but the polymermaterials such as a polyamide compound and a polyimide compounddescribed in paragraphs [0024] to

of WO2005/096041A; the liquid crystal alignment film formed by a liquidcrystal aligning agent having an optical aligned group described inJP2012-155308A; LPP-JP265CP, trade name, manufactured by Rolictechnologies Ltd.; or the like can be used.

In addition, in the present invention, the thickness of the alignmentfilm is not particularly limited, but from the viewpoint of forming anoptically anisotropic film having a uniform film thickness byalleviating the surface roughness present on the support, the thicknessis preferably 0.01 to 10 μm, more preferably 0.01 to 1 μm, and stillmore preferably 0.01 to 0.5 μm.

[Hard Coat Layer]

The optical film of the embodiment of the present invention preferablyhas a hard coat layer in order to impart film physical strength.Specifically, the hard coat layer may be provided on the side of thesupport opposite to the side on which the alignment film is provided(refer to FIG. 1B) or may be provided on the side of the opticallyanisotropic film opposite to the side on which the alignment film isprovided (refer to FIG. 1C).

As the hard coat layer, those described in paragraphs [0190] to [0196]of JP2009-098658A can be used.

[Other Optically Anisotropic Films]

The optical film of the embodiment of the present invention may haveother optically anisotropic films, in addition to the opticallyanisotropic film of the embodiment of the present invention.

That is, the optical film of the embodiment of the present invention mayhave a laminated structure having the optically anisotropic film of theembodiment of the present invention and other optically anisotropicfilms.

Examples of such other optically anisotropic films include opticallyanisotropic films obtained using the above-mentioned polymerizableliquid crystal compound, and are not particularly limited.

Here, the liquid crystal compounds are generally classified into arod-like type and a disk-like type according to the shape thereof.Further, each includes a low molecular type and a high molecular type.The term “high molecular” generally refers to having a degree ofpolymerization of 100 or more (Polymer Physics-Phase TransitionDynamics, by Masao Doi, page. 2, published by Iwanami Shoten,Publishers, 1992). In the present invention, any type of liquid crystalcompound can be used, but a rod-like liquid crystal compound or adiscotic liquid crystal compound (disk-like liquid crystal compound) ispreferably used. Two or more kinds of rod-like liquid crystal compounds,two or more kinds of disk-like liquid crystal compounds, or a mixture ofthe rod-like liquid crystal compound and the disk-like liquid crystalcompound may be used. In order to fix the above-mentioned liquid crystalcompound, it is more preferable that the liquid crystal compound isformed of a rod-like liquid crystal compound or disk-like liquid crystalcompound having a polymerizable group, and it is still more preferablethat the liquid crystal compound has two or more polymerizable groups inone molecule. In the case of a mixture of two or more kinds of theliquid crystal compounds, at least one kind of the liquid crystalcompound preferably has two or more polymerizable groups in onemolecule.

As the rod-like liquid crystal compound, for example, the rod-likeliquid crystal compounds described in claim 1 of JP1999-513019A(JP-H11-513019A) or paragraphs [0026] to [0098] of JP2005-289980A can bepreferably used, and as the discotic liquid crystal compounds, forexample, the discotic liquid crystal compounds described in paragraphs[0020] to [0067] of JP2007-108732A and paragraphs [0013] to [0108] ofJP2010-244038A can be preferably used, but the liquid crystal compoundsare not limited thereto.

[Ultraviolet Absorber]

The optical film of the embodiment of the present invention preferablyincludes an ultraviolet absorber in consideration of the effect ofexternal light (particularly ultraviolet rays), and more preferablyincludes an ultraviolet absorber on a support.

As the ultraviolet absorber, any known ultraviolet absorbers that canexpress ultraviolet absorptivity can be used. Among such ultravioletabsorbers, a benzotriazole-based or hydroxyphenyltriazine-basedultraviolet absorber is preferable since that has high ultravioletabsorptivity and can be used to obtain ultraviolet absorptivity(ultraviolet shielding ability) for use in an electron image displaydevice. Further, a combination of two or more kinds of ultravioletabsorbers having different maximum absorption wavelengths can be used inorder to extend the absorption range of ultraviolet rays.

[Polarizing Plate]

A polarizing plate of an embodiment of the present invention has theabove-mentioned optical film of the embodiment of the present inventionand a polarizer.

[Polarizer]

A polarizer contained in a polarizing plate of an embodiment of thepresent invention is not particularly limited as long as it is a memberhaving a function of converting light into specific linearly polarizedlight, and an absorptive type polarizer and a reflective type polarizer,which are known in the related art, can be used.

An iodine-based polarizer, a dye-based polarizer using a dichroic dye, apolyene-based polarizer, or the like is used as the absorptive typepolarizer. The iodine-based polarizer and the dye-based polarizerencompass a coating type polarizer and a stretching type polarizer, anyof which can be applied, but a polarizer which is manufactured byallowing polyvinyl alcohol to adsorb iodine or a dichroic dye andperforming stretching is preferable.

In addition, examples of a method of obtaining a polarizer by performingstretching and dyeing in a state of a laminated film in which apolyvinyl alcohol layer is formed on a basic material include themethods disclosed in JP5048120B, JP5143918B, JP4691205B, JP4751481B, andJP4751486B, and known technologies related to these polarizers can alsobe preferably used.

A polarizer in which thin films having different birefringence arelaminated, a wire grid type polarizer, a polarizer in which acholesteric liquid crystal having a selective reflection range and a ¼wavelength plate are combined, or the like is used as the reflectivetype polarizer.

Among these, a polarizer including a polyvinyl alcohol-based resin (apolymer including —CH₂—CHOH— as a repeating unit, in particular, atleast one selected from the group consisting of a polyvinyl alcohol andan ethylene-vinyl alcohol copolymer) is preferable from the viewpointthat the adhesiveness is more excellent.

In the present invention, the thickness of the polarizer is notparticularly limited, but is preferably 3 μm to 60 μm, more preferably 5μm to 30 μm, and still more preferably 5 μm to 15 μm.

[Adhesive Layer]

The polarizing plate of the embodiment of the present invention may havean adhesive layer arranged between the optically anisotropic film in theoptical film of the embodiment of the present invention and thepolarizer.

The adhesive layer used for the lamination of the optically anisotropicfilm and the polarizer represents, for example, a substance in which aratio (tan δ=G″/G′) between a storage elastic modulus G′ and a losselastic modulus G″, each measured with a dynamic viscoelastometer, is0.001 to 1.5, and examples thereof include a so-called adhesive orreadily creepable substance. Examples of the adhesive that can be usedin the present invention include a polyvinyl alcohol-based adhesive maybe used, but the adhesive is not limited thereto.

[Image Display Device]

An image display device of an embodiment of the present invention is animage display device having the optical film of the embodiment of thepresent invention or the polarizing plate of the embodiment of thepresent invention.

The display element used in the image display device of the embodimentof the present invention is not particularly limited, and examplesthereof include a liquid crystal cell, an organic electroluminescent(hereinafter abbreviated as “EL”) display panel, and a plasma displaypanel.

Among those, the liquid crystal cell and the organic EL display panelare preferable, and the liquid crystal cell is more preferable. That is,as the image display device of the embodiment of the present invention,a liquid crystal display device using a liquid crystal cell as a displayelement or an organic EL display device using an organic EL displaypanel as a display element is preferable, and the liquid crystal displaydevice is more preferable.

[Liquid Crystal Display Device]

A liquid crystal display device that is an example of the image displaydevice of the embodiment of the present invention is a liquid crystaldisplay device having the above-mentioned polarizing plate of theembodiment of the present invention and a liquid crystal cell.

Furthermore, in the present invention, it is preferable that thepolarizing plate of the embodiment of the present invention is used asthe polarizing plate of the front side, out of the polarizing platesprovided on the both sides of the liquid crystal cell, and it is morepreferable that the polarizing plate of the embodiment of the presentinvention is used as the polarizing plates on the front and rear sides.

Hereinafter, the liquid crystal cell constituting the liquid crystaldisplay device will be described in detail.

<Liquid Crystal Cell>

A liquid crystal cell for use in the liquid crystal display device ispreferably in a vertical alignment (VA) mode, an optically compensatedbend (OCB) mode, an in-plane-switching (IPS) mode, or a twisted nematic(TN) mode, but is not limited thereto.

In the liquid crystal cell in a TN mode, rod-like liquid crystalmolecules are aligned substantially horizontally in a case where novoltage is applied and are further aligned in a twisted manner in arange of 60° to 120°. The liquid crystal cell in a TN mode is most oftenused in a color TFT liquid crystal display device and described in manyliteratures.

In the liquid crystal cell in a VA mode, rod-like liquid crystalmolecules are aligned substantially vertically in a case where novoltage is applied. Examples of the liquid crystal cells in a VA modeinclude (1) a narrowly defined VA mode liquid crystal cell (described inJP1990-176625A (JP-H02-176625A)) in which rod-like liquid crystalmolecules are aligned substantially vertically in a case where novoltage is applied and are aligned substantially horizontally in a casewhere a voltage is applied, (2) a multi-domain VA mode (MVA mode) liquidcrystal cell for enlarging the viewing angle (SID97, described in Digestof tech. Papers (Proceedings) 28 (1997) 845), (3) a liquid crystal cellin a mode (n-ASM mode) in which rod-like liquid crystal molecules arealigned substantially vertically in a case where no voltage is appliedand are aligned in twisted multi-domain alignment in a case where avoltage is applied (Proceedings of Japanese Liquid Crystal Conference,58 and 59 (1998)), and (4) a liquid crystal cell in a SURVIVAL mode(presented in LCD International 98). Further, the liquid crystal cellmay be of any of a patterned vertical alignment (PVA) type, an opticalalignment type, and a polymer-sustained alignment (PSA) type. Details ofthese modes are described in detail in JP2006-215326A andJP2008-538819A.

In the liquid crystal cell in an IPS mode, rod-like liquid crystalmolecules are aligned substantially parallel with respect to a substrateand application of an electric field parallel to the substrate surfacecauses the rod-like liquid crystal molecules to respond planarly. TheIPS mode displays black in a case where no electric field is applied anda pair of upper and lower polarizing plates have absorption axes whichare orthogonal to each other. A method of improving the viewing angle byreducing light leakage during black display in an oblique directionusing an optical compensation sheet is disclosed in JP1998-054982A(JP-H10-054982A), JP1999-202323A (JP-H11-202323A), JP1997-292522A(JP-H09-292522A), JP1999-133408A (JP-H11-133408A), JP1999-305217A(JP-H11-305217A), JP1998-307291A (JP-H10-307291 A), and the like.

[Organic EL Display Device]

Suitable examples of the organic EL display device which is an exampleof the image display device of the embodiment of the present inventioninclude an aspect which includes, from the visible side, the polarizingplate of the embodiment of the present invention, a plate having a λ/4function (hereinafter referred to also as “Δ/4 plate”) and an organic ELdisplay panel in this order.

Here, an expression, a “plate having a λ/4 function” refers to a platehaving a function of converting linearly polarized light at a specificwavelength into circularly polarized light (or circularly polarizedlight into linearly polarized light). Specific examples of an aspect inwhich a λ/4 plate is of a single layer structure include a stretchedpolymer film, and a retardation film in which an optically anisotropicfilm having a λ/4 function is provided on a support, and specificexamples of an embodiment in which a λ4 plate is of a multilayerstructure include a broadband λ/4 plate in which the λ4 plate and a λ/2plate are laminated on each other.

Furthermore, the organic EL display panel is a display panel configuredusing an organic EL device in which an organic light emitting layer(organic electroluminescent layer) is sandwiched between electrodes(between a cathode and an anode). The configuration of the organic ELdisplay panel is not particularly limited but any known configuration isadopted.

The image display device of the embodiment of the present invention ispreferably an organic EL display device including an organic EL displaypanel and a circularly polarizing plate arranged on the organic ELdisplay panel.

In particular, in the present invention, an aspect in which thecircularly polarizing plate includes a polarizer and the above-mentionedoptical film of the embodiment of the present invention is morepreferable, and an aspect in which the circularly polarizing plate has apolarizer and an optical film having two or more layers of the opticallyanisotropic films, in which at least one of the layers is a positive Aplate and at least one of the other layers is a positive C plate, isstill more preferable.

EXAMPLES

Hereinafter, the present invention will be described in more detail withreference to Examples. The materials, the amounts of materials used, theproportions, the treatment details, the treatment procedure, and thelike shown in Examples below may be modified, as appropriate, as long asthe modifications do not depart from the spirit of the presentinvention. Therefore, the scope of the present invention should not beconstrued as being limited to Examples shown below.

[Polymerizable Liquid Crystal Compound]

In the preparation of polymerizable liquid crystal compositions, thefollowing polymerizable liquid crystal compounds 1 to 7 were prepared.

<Synthesis of Polymerizable Liquid Crystal Compound 1 (ReverseDispersion Liquid Crystal 1)>

According to the following scheme, compounds represented by Formulae Ato C (hereinafter also simply referred to as compounds A to C,respectively) were synthesized.

(Synthesis of Compound A)

The synthesis of the compound A was performed by the method described in“Journal of Organic Chemistry” (2004); 69(6); p. 2164-2177.

(Synthesis of Compound B)

30.0 g (0.0916 mol) of the compound A, 19.8 g (0.137 mol) of Meldrum'sacid, and 200 mL of N-methyl-2-pyrrolidone (NMP) were mixed and stirredat 55° C. for 2 hours.

Thereafter, the mixture was cooled to room temperature, 200 mL of waterwas added to the mixture, and the precipitated crystal was filtered.

The obtained crystal was washed with a mixed solution of water and NMPat 1:1 to obtain 28.4 g (0.0870 mol) of a compound B (yield: 95%).

(Compound C)

51.5 g (0.158 mol) of the compound B and 315 mL of THF were mixed, and395 mL (0.789 mol) of a 2 M aqueous sodium hydroxide solution was addeddropwise thereto under ice-cooling.

Subsequently, the mixture was warmed to room temperature and stirred for2 hours, and then 263 mL (0.789 mol) 3 N aqueous hydrochloric acid wasadded dropwise thereto under ice-cooling.

Subsequently, 300 mL of water and 180 mL of isopropyl alcohol (IPA) wereadded thereto and the precipitated solid was filtered.

The obtained solid was stirred with acetonitrile, suspended, and thenfiltered to obtain 25 g (0.0868 mol) of a compound C (yield: 55%).

Subsequently, according to the following scheme, a compound Drepresented by Formula D was synthesized.

(Synthesis of Compound D)

50 g (0.175 mol) of the compound C, BHT (1.9 g, 8.74 mmol), 300 mL ofTHF, and 150 mL of N,N-dimethylacetamide (DMAc) were mixed, and 87.3 g(0.734 mol) of thionyl chloride was added dropwise thereto underice-cooling.

Subsequently, the mixture was stirred for 2 hours under ice-cooling, andthen 126 g (0.874 mol) of 4-hydroxybutylacrylic acid ester was addeddropwise thereto.

Subsequently, the mixture was warmed to room temperature, the mixturewas stirred for 2 hours and then extracted by the addition of 400 mL of5% saline, 100 mL of ethyl acetate, and 200 mL of tetrahydrofuran (THF).

The organic layer was washed twice with 200 mL of 10% saline, then theorganic layer was dried over magnesium sulfate, and the solvent wasdistilled off under reduced pressure. The obtained crude product wasstirred with acetonitrile, suspended, and filtered to obtain 57 g (0.107mol) of a compound D (yield: 61%).

(Synthesis of Reverse Dispersion Liquid Crystal 1)

According to the following scheme, 12.7 g (0.107 mmol) of thionylchloride was added to a solution of 22.1 g (0.0928 mol) of a compound Erepresented by Formula E in 40 ml of toluene, and a catalytic amount ofN,N-dimethylformamide was added thereto. The mixture was warmed to 65°C. as it was and then stirred for 2 hours, and the solvent was distilledoff.

Subsequently, 25 g (0.0464 mol) of the compound D, BHT (0.51 g, 2.32mmol), and THF (125 mL) were added to the mixture, and 10.3 g (0.102mol) of triethylamine was added dropwise thereto under ice-cooling.

Subsequently, the mixture was warmed to room temperature, stirred for 2hours, and then extracted by the addition of 100 ml of 1 M aqueoushydrochloric acid and 40 ml of ethyl acetate.

The organic layer was washed with 10% saline, then 400 ml of methanolwas added to the organic layer, and the precipitated solid was filteredto obtain 38 g (0.0389 mol) of a reverse dispersion liquid crystal 1represented by Formula 1 (yield: 84%).

<Synthesis of Polymerizable Liquid Crystal Compound 2 (ReverseDispersion Liquid Crystal 2)>

According to the method described in paragraphs [0462] to [0477] ofJP2011-207765A, a reverse dispersion liquid crystal 2 represented byFormula 2 was synthesized.

<Synthesis of Polymerizable Liquid Crystal Compound 3 (ReverseDispersion Liquid Crystal 3)>

According to the method described in paragraphs [0205] to [0217] ofWO2014/010325A, a reverse dispersion liquid crystal 3 represented byFormula 3 was synthesized.

<Synthesis of Polymerizable Liquid Crystal Compound 4 (ForwardDispersion Liquid Crystal 1)>

In accordance with the method described in Reference 1 (Makromol. Chem.190, page 59 (1991)), a forward dispersion liquid crystal 1 representedby the following formula was synthesized.

<Synthesis of Polymerizable Liquid Crystal Compound 5 (ReverseDispersion Liquid Crystal 4)>

A side-chain carboxylic acid F represented by Formula F and a phenol Grepresented by Formula C were synthesized, and a reverse dispersionliquid crystal 4 represented by Formula 5 was synthesized by thefollowing route.

(Synthesis of Side-Chain Carboxylic Acid F)

According to the compound (I-4C) described in JP2016-081035A, aside-chain carboxylic acid F of the reverse dispersion liquid crystal 4was synthesized.

¹H-NMR (Nuclear Magnetic Resonance) of the obtained side-chaincarboxylic acid F is shown below.

¹H-NMR (solvent: CDCl₃) δ (ppm):

[Major Isomer]

1.27 (d, 3H), 1.45-1.73 (m, 4H), 2.10-2.32 (m, 4H), 2.32-2.45 (m, 1H),2.48-2.70 (m, 1H), 2.62 (s, 4H), 2.93 (t, 2H), 4.15 (dd, 1H), 4.25 (dd,1H), 4.29 (t, 2H), 5.20 (m, 1H), 5.85 (dd, 1H), 6.13 (dd, 1H), 6.42 (dd,1H), 6.95-7.06 (m, 2H), 7.16-7.25 (m, 2H)

[Minor Isomer]

1.29 (d, 3H), 1.45-1.73 (m, 4H), 2.10-2.32 (m, 4H), 2.32-2.45 (m, 1H),2.48-2.70 (m, 1H), 2.62 (s, 4H), 2.93 (t, 2H), 4.13 (dd, 1H), 4.22 (dd,1H), 4.29 (t, 2H), 5.20 (m, 1H), 5.84 (dd, 1H), 6.11 (dd, 1H), 6.41 (dd,1H), 6.95-7.06 (m, 2H), 7.16-7.25 (m, 2H)

(Synthesis of Phenol G)

The synthesis of the phenol G can be performed with reference to themethod described in Justus Liebigs Annalen der Chemie, 726, 103-109(1969).

In a nitrogen stream, 21.79 g (334 mmol) of potassium hydroxide at acontent of 86% was dissolved in 70 ml of isopropyl alcohol and 85 ml ofwater. To this solution was added a solution obtained by dissolving11.03 g (167 mmol) of malononitrile in 12 ml of isopropyl alcohol at aninner temperature of 5° C. or lower while stirring the mixture underice-cooling.

Subsequently, 13.35 g (175 mmol) of carbon disulfide was added dropwisethereto at an inner temperature of 10° C. or lower, and then the mixturewas stirred for 30 minutes under ice-cooling. To this reaction liquidwas slowly added dropwise a mixed solution of 36.46 g (338 mmol) of1,4-benzoquinone, 21.96 ml (384 mmol) of acetic acid, and 200 ml ofacetone while keeping the inner temperature at 2° C. or lower. Themixture was stirred at the same temperature for 30 minutes and thenwarmed to 25° C., and 365 ml of water was added thereto.

Subsequently, the precipitated crystal was collected by filtration andwashed with 835 ml of water and then with a mixed solution ofwater/acetone (90 ml/90 ml) to obtain a crude product.

Subsequently, the crude product and 100 ml of THF were mixed and stirredin a nitrogen stream, and warmed to 40° C., and then 150 ml of water wasadded dropwise thereto at 40° C.

Thereafter, the mixture was cooled to 5° C. to precipitate a crystal,followed by stirring at 5° C. for 1 hour. The precipitated crystal wascollected by filtration, washed with a mixed solution of THF/water (40ml/120 ml), and then dried at 60° C. under reduced pressure to obtain31.3 g (yield: 75%) of a phenol G as a pale yellow solid.

¹H-NMR of the obtained phenol G is shown below.

¹H-NMR (DMSO-d₆) δ (ppm): 6.80 (s, 2H), 10.51 (s, 2H)

(Synthesis of Reverse Dispersion Liquid Crystal 4)

According to the compound (I-4) described in JP2016-081035A, a reversedispersion liquid crystal 4 was synthesized.

¹H-NMR of the obtained reverse dispersion liquid crystal 4 is shownbelow.

¹H-NMR (solvent: CDCl₃) δ (ppm):

[Major Isomer]

1.27 (d, 6H), 1.56-1.79 (m, 8H), 2.22-2.40 (m, 8H), 2.55-2.75 (m, 4H),2.62 (s, 8H), 2.94 (t, 4H), 4.15 (dd, 2H), 4.25 (dd, 2H), 4.28 (t, 4H),5.20 (m, 2H), 5.86 (dd, 2H), 6.13 (dd, 2H), 6.43 (dd, 2H), 6.99-7.06 (m,4H), 7.20-7.25 (m, 4H), 7.32 (s, 2H)

[Minor Isomer]

1.29 (d, 6H), 1.56-1.79 (m, 8H), 2.22-2.40 (m, 8H), 2.55-2.75 (m, 4H),2.62 (s, 8H), 2.94 (t, 4H), 4.12 (dd, 2H), 4.22 (dd, 2H), 4.28 (t, 4H),5.20 (m, 2H), 5.84 (dd, 2H), 6.11 (dd, 2H), 6.41 (dd, 2H), 6.99-7.06 (m,4H), 7.20-7.25 (m, 4H), 7.32 (s, 2H)

<Synthesis of Polymerizable Liquid Crystal Compound 6 (ReverseDispersion Liquid Crystal 5)>

A side-chain carboxylic acid F represented by Formula F and a phenol Hrepresented by Formula H were synthesized, and a reverse dispersionliquid crystal 5 represented by Formula 6 was synthesized by thefollowing route.

(Synthesis of Phenol H)

In a nitrogen stream, 19.57 g (300 mmol) of potassium hydroxide at acontent of 86% was dissolved in 60 ml of isopropyl alcohol and 75 ml ofwater. To this solution was added a solution obtained by dissolving 9.91g (150 mmol) of malononitrile in 10.5 ml of isopropyl alcohol at aninner temperature of 5° C. or lower while stirring the mixture underice-cooling.

Subsequently, 11.42 g (150 mmol) of carbon disulfide was added dropwisethereto at an inner temperature of 10° C. or lower, and then the mixturewas stirred for 30 minutes under ice-cooling. Subsequently, 2.57 ml (45mmol) of acetic acid was added to adjust the pH of the reaction liquidto 6. To this reaction liquid was slowly added dropwise a mixed solutionof 36.26 g (298 mmol) of p-toluquinone, 16.98 ml (298 mmol) of aceticacid, and 150 ml of acetone while keeping the inner temperature at 5° C.or lower. The mixture was stirred at the same temperature for 30 minutesand then warmed to 50° C., and 395 ml of water was added thereto.

The mixture was stirred for 30 minutes, then the temperature was loweredto 15° C., and the precipitated crystal was collected by filtration andwashed with 790 ml of water to obtain a crude product.

Subsequently, the crude product, 155 ml of acetonitrile, and 155 ml ofwater were mixed in a nitrogen stream, stirred at room temperature for 1hour, and then cooled to 5° C., and the mixture was further stirred for30 minutes. The precipitated crystal was collected by filtration, washedwith a mixed solution of acetonitrile/water (50 ml/60 ml) which had beenice-cooled, and then dried at 60° C. under reduced pressure to obtain32.6 g (yield: 83%) of a phenol H as a yellow solid.

¹H-NMR of the obtained phenol H is shown below.

¹H-NMR (solvent: DMSO-d₆) δ (ppm): 2.19 (s, 3H), 6.71 (s, 1H), 9.60 (brs, 1H), 10.55 (br s, 1H)

(Synthesis of Reverse Dispersion Liquid Crystal 5)

According to the compound (IV-4) described in JP2016-081035A, a reversedispersion liquid crystal 5 was synthesized.

¹H-NMR of the obtained reverse dispersion liquid crystal 5 is shownbelow.

¹H-NMR (solvent: CDCl₃) δ (ppm):

[Major Isomer]

1.27 (d, 6H), 1.56-1.79 (m, 8H), 2.22 (s, 3H), 2.22-2.40 (m, 8H),2.55-2.75 (m, 4H), 2.62 (s, 8H), 2.94 (t, 4H), 4.15 (dd, 2H), 4.25 (dd,2H), 4.28 (t, 4H), 5.20 (m, 2H), 5.86 (dd, 2H), 6.13 (dd, 2H), 6.43 (dd,2H), 6.99-7.06 (m, 4H), 7.20-7.25 (m, 4H), 7.25 (s, 1H)

[Minor Isomer]

1.29 (d, 6H), 1.56-1.79 (m, 8H), 2.22 (s, 3H), 2.22-2.40 (m, 8H),2.55-2.75 (m, 4H), 2.62 (s, 8H), 2.94 (t, 4H), 4.12 (dd, 2H), 4.22 (dd,2H), 4.28 (t, 4H), 5.20 (m, 2H), 5.84 (dd, 2H), 6.11 (dd, 2H), 6.41 (dd,2H), 6.99-7.06 (m, 4H), 7.20-7.25 (m, 4H), 7.25 (s, 1H)

<Synthesis of Polymerizable Liquid Crystal Compound 7 (ForwardDispersion Liquid Crystal 2)>

According to the method described in JP6086884B, a forward dispersionliquid crystal 2 represented by the following formula was synthesized.

<Measurement of pKa>

A pKa (first acid dissociation constant) of the compound (for example,the compound D in the polymerizable liquid crystal compound 1) used forthe formation of a core portion of each polymerizable liquid crystalcompound was determined by computation using the above-mentionedsoftware package 1. The pKa is shown in Table 1.

[Additives]

In the preparation of the polymerizable liquid crystal composition, thefollowing various additives were prepared.

<Synthesis of Aromatic Polyether-Based Compound 1>

The aromatic polyether-based compound 1 is an aromatic diether-basedcompound (aromatic diether 1) represented by Formula (C-I), and wassynthesized with reference to the method described in Synthesis Example1 of JP1987-045545B (JP-S62-045545B).

<Synthesis of Aromatic Polyether-Based Compound 2>

The aromatic polyether-based compound 2 is an aromatic diether-basedcompound (aromatic diether 2) represented by Formula (E-I), and wassynthesized by the following method.

20 mL of a dimethylacetamide solvent was put into a 300-mL flask,DL-α-tocopherol (4.31 g, 10 mmol), a halogen compound (a compoundrepresented by Formula (HA-1), 3.37 g, 11 mmol), and 28% sodiummethoxide (2.12 g, 11 mmol) as a base were added thereto, and themixture was stirred at an inner temperature of 80° C. for 3 hours.Thereafter, water was added thereto, and the mixture was subjected toliquid separation ethyl acetate, dried over magnesium sulfate, and thenconcentrated to obtain 5.5 g of a compound (E-I).

<Synthesis of Aromatic Polyether-Based Compound 3>

The aromatic polyether-based compound 3 is an aromatic diether-basedcompound (aromatic diether 3) represented by Formula (D-I), comprises astructure similar to the compound represented by (27) described inJP1987-010420B (JP-S62-010420B), and was synthesized by the followingroute.

[Other Additives]

<Synthesis of Amine-Based Compound 1>

The amine-based compound 1 is an amine-based compound represented by thefollowing formula, and was synthesized with reference to the methoddescribed in WO2005/051915A.

<Hindered Amine-Based Compound>

-   -   CHIMASSORB NOR 2020FDL (trade name, manufactured by BASF)    -   TINUVIN 765 (trade name, manufactured by BASF)    -   TINUVIN 770DF (trade name, manufactured by BASF)

<Hindered Phenol-Based Compound>

-   -   Irganox 1035FF (trade name, manufactured by BASF)

[Polymerization Initiator]

As the polymerization initiator, a compound represented by the followingformula (the exemplary compound (A-1) described in JP2011-158655A) wasprepared.

[Air Interface Alignment agent (Leveling Agent)]

As the air interface alignment agent, a compound represented by thefollowing formula (the leveling agent T-1 described in JP2016-053709A)was prepared.

[Solvent]

As the solvent, chloroform was prepared.

Examples 1 to 19 and Comparative Examples 1 to 22

[Preparation of Polymerizable Liquid Crystal Composition]

A polymerizable liquid crystal compound, a polymerization initiator, anair interface alignment agent, and an additive were dissolved in asolvent (chloroform) to prepare each of polymerizable liquid crystalcompositions of Examples and Comparative Examples. The type and theblend amount of each of the components are shown as in Table 1 below.Further, in Example 19, a combination of a reverse dispersion liquidcrystal 4, a reverse dispersion liquid crystal 5, and a forwarddispersion liquid crystal 1 was used as the polymerizable liquid crystalcompound as shown Table 1 below, but the addition amounts thereof were42:42:16 in terms of a mass ratio. In addition, in Table 1 below, the“addition amount ratio” means a content (parts by mass) of an additivewith respect to 100 parts by mass of the polymerizable liquid crystalcompound in the polymerizable liquid crystal composition.

Furthermore, each of the polymerizable liquid crystal compositionsexcluding only additives from the composition of each of thepolymerizable liquid crystal compositions of Examples and ComparativeExamples as a reference was prepared.

[Light Fastness Test]

<Manufacture of Sample>

By a spin-coating method (amount of a polymerizable liquid crystalcomposition applied: 80 μL, rotation speed: 1,500 rpm), thepolymerizable liquid crystal composition was applied onto a glasssubstrate (EAGLE XG: manufactured by Corning Incorporated) cut to2.5×3.0 cm and dried to manufacture a coating film on the glasssubstrate.

Subsequently, the coating film was warmed to 160° C. on a hot plate andirradiated by an ultraviolet irradiating device (manufactured by NipponBunka Seiko Co., Ltd.) at an irradiation dose of 500 mJ to manufacture acured film.

<Measurement of Absorbance of Cured Film before Light Fastness Test>

An absorbance A of a cured film at an absorption maximum wavelength(absorbance of the cured film before a light fastness test) was measuredusing an infrared-visible measuring device (trade name “UV-3150”,manufactured by Shimadzu Corporation). Specifically, a baselinecorrection was performed using the glass substrate on which thepolymerizable liquid crystal composition had not been applied, and thenan absorbance A of the cured film at the absorption maximum wavelengthwas measured.

<Measurement of Absorbance of Cured Film after Light Fastness Test>

First, the glass substrate was set in a Xenon irradiator (SX75manufactured by Suga Test Instruments Co., Ltd.) so that the cured filmof the polymerizable liquid crystal composition became a surface to beirradiated, and a sample was irradiated under a condition of 150 W/m² ata distance of 290 mm from a light source for 2 hours using a #275filter, thereby obtaining a cured film after the light fastness test.

Subsequently, an absorbance B (absorbance of the cured film after thelight fastness test) of the cured film after the light fastness at anabsorption maximum wavelength was measured using an infrared-visiblemeasuring device (trade name “UV-3150”, manufactured by ShimadzuCorporation).

<Evaluation of Light Fastness>

Using the cured film of the polymerizable liquid crystal composition asa reference (containing no additive), the above-mentioned absorbance Aand absorbance B were measured, and a light fastness residual rate X (%)was calculated by the following equation.

Similarly, using the cured film of each of the polymerizable liquidcrystal compositions of Examples and Comparative Examples, theabove-mentioned absorbance A and absorbance B were measured, and a lightfastness residual rate (%) was calculated by the following equation.Light fastness residual rate (%)=(Absorbance B/Absorbance A)×100

From the values of the light fastness residual rate X and the lightfastness residual rate Y, each obtained as described above, a lightfastness improvement rate was calculated by the following equation, andthe light fastness was evaluated in accordance with the followingevaluation standard.Light fastness improvement rate (%)=Light fastness residual rate Y-Lightfastness residual rate X

A: The light fastness improvement rate is 10% or more.

B: The light fastness residual rate is more than 5% and less than 10%.

C: The light fastness improvement rate is more than 0% and 5% or less.

D: The light fastness improvement rate is 0% or less.

<Evaluation Results>

The results of the evaluation tests above are shown in Table 1 below.

TABLE 1 Air interface Polymerization alignment agent Solvent EvaluationPolymerizable liquid crystal compound Additive initiator AdditionAddition results Type pKa calculated Addition amount (g) Type Additionamount (g) Addition ratio Addition amount (g) amount (g) amount (g)Light fastness Example 1 Reverse dispersion 8.47 0.1 Aromatic diether 10.001 1 0.0005 0.0002 3.18 B liquid crystal 1 Example 2 Reversedispersion 8.47 0.1 Aromatic diether 1 0.005 5 0.0005 0.0002 3.3 Aliquid crystal 1 Example 3 Reverse dispersion 8.47 0.1 Aromatic diether1 0.01 10 0.0005 0.0002 3.46 A liquid crystal 1 Example 4 Reversedispersion 8.47 0.1 Aromatic diether 2 0.001 1 0.0005 0.0002 3.18 Aliquid crystal 1 Example 5 Reverse dispersion 8.47 0.1 Aromatic diether2 0.005 5 0.0005 0.0002 3.3 A liquid crystal 1 Example 6 Reversedispersion 8.47 0.1 Aromatic diether 2 0.01 10 0.0005 0.0002 3.46 Aliquid crystal 1 Example 7 Reverse dispersion 8.47 0.1 Aromatic diether2 0.02 20 0.0005 0.0002 3.77 A liquid crystal 1 Example 8 Reversedispersion 8.47 0.1 Aromatic diether 3 0.001 1 0.0005 0.0002 3.18 Bliquid crystal 1 Example 9 Reverse dispersion 8.47 0.1 Aromatic diether3 0.005 5 0.0005 0.0002 3.3 A liquid crystal 1 Example 10 Reversedispersion 8.47 0.1 Aromatic diether 3 0.01 10 0.0005 0.0002 3.46 Aliquid crystal 1 Example 11 Reverse dispersion 8.47 0.1 Aromatic diether3 0.02 20 0.0005 0.0002 3.77 A liquid crystal 1 Example 12 Reversedispersion 8.82 0.1 Aromatic diether 1 0.005 5 0.0005 0.0002 3.3 Aliquid crystal 2 Example 13 Reverse dispersion 8.82 0.1 Aromatic diether2 0.005 5 0.0005 0.0002 3.3 A liquid crystal 2 Example 14 Reversedispersion 8.82 0.1 Aromatic diether 3 0.005 5 0.0005 0.0002 3.3 Aliquid crystal 2 Example 15 Reverse dispersion 9.56 0.1 Aromatic diether1 0.005 5 0.0005 0.0002 3.3 B liquid crystal 3 Example 16 Reversedispersion 9.56 0.1 Aromatic diether 2 0.005 5 0.0005 0.0002 3.3 Bliquid crystal 3 Example 17 Reverse dispersion 8.3 0.1 Aromatic diether1 0.005 5 0.0005 0.0002 3.3 B liquid crystal 4 Example 18 Reversedispersion 8.71 0.1 Aromatic diether 1 0.005 5 0.0005 0.0002 3.3 Bliquid crystal 5 Example 19 Reverse dispersion — 0.1 Aromatic diether 10.005 5 0.0005 0.0002 3.3 B liquid crystal 4 Reverse dispersion liquidcrystal 5 Forward dispersion liquid crystal 2 Comparative Reversedispersion 8.47 0.1 Amine-based 0.001 1 0.0005 0.0002 3.18 C Example 1liquid crystal 4 compound 1 Comparative Reverse dispersion 8.47 0.1Amine-based 0.005 5 0.0005 0.0002 3.3 D Example 2 liquid crystal 1compound 1 Comparative Reverse dispersion 8.47 0.1 Amine-based 0.01 100.0005 0.0002 3.46 D Example 3 liquid crystal 1 compound 1 ComparativeReverse dispersion 8.47 0.1 CHIMASORB NOR 0.001 1 0.0005 0.0002 3.18 DExample 4 liquid crystal 1 2020FDL Comparative Reverse dispersion 8.470.1 CHIMASORB NOR 0.005 5 0.0005 0.0002 3.3 C Example 5 liquid crystal 12020FDL Comparative Reverse dispersion 8.47 0.1 CHIMASORB NOR 0.01 100.0005 0.0002 3.46 C Example 6 liquid crystal 1 2020FDL ComparativeReverse dispersion 8.47 0.1 TINUVIN 765 0.001 1 0.0005 0.0002 3.18 CExample 7 liquid crystal 1 Comparative Reverse dispersion 8.47 0.1TINUVIN 765 0.005 5 0.0005 0.0002 3.3 D Example 8 liquid crystal 1Comparative Reverse dispersion 8.47 0.1 TINUVIN 765 0.01 10 0.00050.0002 3.46 C Example 9 liquid crystal 1 Comparative Reverse dispersion8.47 0.1 TINUVIN 770DF 0.001 1 0.0005 0.0002 3.18 D Example 10 liquidcrystal 1 Comparative Reverse dispersion 8.47 0.1 TINUVIN 770DF 0.005 50.0005 0.0002 3.3 D Example 11 liquid crystal 1 Comparative Reversedispersion 8.47 0.1 TINUVIN 770DF 0.01 10 0.0005 0.0002 3.46 C Example12 liquid crystal 1 Comparative Reverse dispersion 8.47 0.1 Irganox1035FF 0.001 1 0.0005 0.0002 3.18 C Example 13 liquid crystal 1Comparative Reverse dispersion 8.47 0.1 Irganox 1035FF 0.005 5 0.00050.0002 3.3 D Example 14 liquid crystal 1 Comparative Reverse dispersion8.47 0.1 Irganox 1035FF 0.01 10 0.0005 0.0002 3.46 D Example 15 liquidcrystal 1 Comparative Reverse dispersion 8.82 0.1 Amine-based 0.005 50.0005 0.0002 3.3 D Example 16 liquid crystal 2 compound 1 ComparativeReverse dispersion 8.82 0.1 TINUVIN 765 0.005 5 0.0005 0.0002 3.3 DExample 17 liquid crystal 2 Comparative Reverse dispersion 8.82 0.1Irganox 1035FF 0.005 5 0.0005 0.0002 3.3 D Example 18 liquid crystal 2Comparative Reverse dispersion 9.56 0.1 Amine-based 0.005 5 0.00050.0002 3.3 D Example 19 liquid crystal 3 compound 1 Comparative Reversedispersion 9.56 0.1 TINUVIN 765 0.005 5 0.0005 0.0002 3.3 D Example 20liquid crystal 3 Comparative Reverse dispersion 9.56 0.1 Irganox 1035FF0.005 5 0.0005 0.0002 3.3 D Example 21 liquid crystal 3 ComparativeForward dispersion 10.8 0.1 Aromatic diether 1 0.005 5 0.0005 0.0002 3.3D Example 22 liquid crystal 1

From the evaluation results shown in Table 1, it was found that in acase where a polymerizable liquid crystal composition containing anaromatic polyether-based compound is used as an additive, it is possibleto form a film having excellent light fastness (Examples).

In contrast, it was found that in a case where a polymerizable liquidcrystal composition containing no aromatic polyether-based compound isused as an additive, the light fastness of a film thus obtained isdeteriorated (Comparative Examples 1 to 21).

In addition, it was found that in a case where a polymerizable liquidcrystal compound having forward wavelength dispersion properties isused, the light fastness of a film thus obtained is deteriorated evenwith the addition of an aromatic polyether-based compound (ComparativeExample 22).

[Preparation of Composition for Optical Alignment Film]

By a method which will be described later, a polymer, a low molecularcompound, a crosslinking agent, and a crosslinking catalyst wassynthesized or prepared.

<Synthesis of Polymer>

100.0 parts by mass of 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 500parts by mass of methyl isobutyl ketone, and 10.0 parts by mass oftriethylamine were introduced into a reaction vessel comprising astirrer, a thermometer, a dropping funnel, and a reflux condenser, andmixed at room temperature. Subsequently, 100 parts by mass of deionizedwater was added dropwise from the dropping funnel for 30 minutes andthen allowed to undergo a reaction at 80° C. for 6 hours while mixingunder reflux. After completion of the reaction, the organic phase wasextracted and washed until water after washing with a 0.2%-by-massaqueous ammonium nitrate solution became neutral, and then the solventand water were distilled off under reduced pressure to obtain anepoxy-containing polyorganosiloxane as a viscous transparent liquid.

The epoxy-containing polyorganosiloxane was subjected to ¹H-NMRanalysis, and it was thus found that a peak based on an oxiranyl grouparound a chemical shift (δ)=3.2 ppm was obtained as for a theoreticalstrength, and a side reaction of the epoxy group did not occur duringthe reaction. The weight-average molecular weight Mw and the epoxyequivalents of the epoxy-containing polyorganosiloxane were 2,200 and186 g/mol, respectively.

Next, 10.5 parts by mass of the epoxy-containing polyorganosiloxaneobtained above, 0.4 parts by mass of an acrylic group-containingcarboxylic acid (manufactured by Toagosei Co., Ltd., trade name “AronixM-5300”, acrylic acid ω-carboxypolycaprolactone (polymerization degreen≈2)), 20 parts by mass of butyl acetate, 0.5 parts by mass of thecinnamic acid derivative obtained by the method of Synthesis Example 1of JP2015-026050A, 0.5 parts by mass of tetrahydrofuroic acid(manufactured by Wako Pure Chemical Industries, Ltd.), and 0.3 parts bymass of tetrabutylammonium bromide were introduced into a 100-mLthree-neck flask and stirred at 90° C. for 12 hours. After completion ofthe reaction, the mixture was diluted with butyl acetate in the sameamount (mass) as that of the reaction liquid and washed three times withwater. The solution was concentrated and twice subjected to an operationof dilution with butyl acetate, thereby finally obtaining a solutionincluding a polyorganosiloxane (polymer) containing an optically alignedgroup. The weight-average molecular weight Mw of the polymer was 10,000.

<Low Molecular Compound>

A low molecular compound represented by Formula B (NOMCORT TAB,manufactured by Nisshin OilliO Group) was used.

<Crosslinking Agent>

As the crosslinking agent, a polyfunctional epoxy compound (EPOLEADGT401, manufactured by Daniel Chemical Industries, Ltd.) was used.

<Crosslinking Catalyst>

A thermal acid generator (San-Aid SI-60, manufactured by SanshinChemical Industry Co., Ltd.) was used as the crosslinking catalyst forthe purpose of accelerating crosslinking.

<Preparation of Composition for Optical Alignment Film>

4.6 parts by mass of the above-mentioned polymer, 0.8 parts by mass ofthe above-mentioned low molecular compound, 0.8 parts by mass of theabove-mentioned crosslinking agent, and 0.8 parts by mass of theabove-mentioned crosslinking catalyst were added with respect to 100parts by mass of butyl acetate, stirred, and then filtered through afilter having a pore diameter of 1 μm to obtain a liquid crystalaligning agent having a concentration of the solid content of 7.5% bymass. Further, in the obtained liquid crystal aligning agent, componentssuch as a polymer were dissolved in a solvent in the same amount as theaddition amount.

Examples 20 to 23 and Comparative Example 23

[Preparation of Coating Liquid for Forming Optically Anisotropic Film]

Coating liquids 1 to 5 for forming an optically anisotropic film, whichhave the following compositions, were prepared.

Coating liquid 1 for forming an optically anisotropic film Reversedispersion liquid crystal 1 95.00 parts by mass  Aromatic diether 1 5.00parts by mass Polymerization initiator A-1 below 0.05 parts by massLeveling agent T-1 below 0.20 parts by mass Cyclopentanone 424.8 partsby mass 

Coating liquid 2 for forming an optically anisotropic film Reversedispersion liquid crystal 2 95.00 parts by mass  Aromatic diether 1 5.00parts by mass Polymerization initiator A-1 0.05 parts by mass Levelingagent T-1 0.20 parts by mass Cyclopentanone 424.8 parts by mass 

Coating liquid 3 for forming an optically anisotropic film Reversedispersion liquid crystal 3 95.00 parts by mass Aromatic diether 1  5.00parts by mass Polymerization initiator A-1  0.05 parts by mass Levelingagent T-1  0.20 parts by mass Cyclopentanone 424.8 parts by mass

Coating liquid 4 for forming an optically anisotropic film Reversedispersion liquid crystal 4 40.00 parts by mass Reverse dispersionliquid crystal 5 40.00 parts by mass Forward dispersion liquid crystal 215.00 parts by mass Aromatic diether 1  5.00 parts by massPolymerization initiator A-1  0.50 parts by mass Leveling agent T-1 0.20 parts by mass Hisolve MTEM (manufactured by TOHO  2.00 parts bymass Chemical Industry Co., Ltd.) NKester A-200 (manufactured by ShinNakamura  1.00 part by mass chemical Co., Ltd.) Methyl ethyl ketone424.8 parts by mass

Coating liquid 5 for forming an optically anisotropic film Forwarddispersion liquid crystal 1 95.00 parts by mass Aromatic diether 1  5.00parts by mass Polymerization initiator A-1  0.50 parts by mass Levelingagent T-1  0.20 parts by mass Hisolve MTEM (manufactured by TOHO  2.00parts by mass Chemical Industry Co., Ltd.) NKester A-200 (manufacturedby Shin Nakamura  1.00 part by mass chemical Co., Ltd.) Methyl ethylketone 424.8 parts by mass

[Manufacture of Cellulose Acylate Film 1]

<Manufacture of Core Layer Cellulose Acylate Dope>

The following composition was put into a mixing tank and stirred todissolve the respective components to prepare a cellulose acetatesolution for use as a core layer cellulose acylate dope.

Core layer cellulose acylate dope Cellulose acetate having a degree ofsubstitution 100 parts by mass with acetyl of 2.88 Polyester compound Bdescribed in Examples  12 parts by mass of JP2015-227955A Compound Fbelow  2 parts by mass Methylene chloride (first solvent) 430 parts bymass Methanol (second solvent)  64 parts by mass

<Manufacture of Outer Laver Cellulose Acylate Dope>

10 parts by mass of the following matting solution was added to 90 partsby mass of the core layer cellulose acylate dope to prepare a celluloseacetate solution which is used as an outer layer cellulose acylate dope.

Matting solution Silica particles having an average particle size of  2parts by mass 20 nm (AEROSIL R972, manufactured by Nippon Aerosil Co.,Ltd.) Methylene chloride (first solvent) 76 parts by mass Methanol(second solvent) 11 parts by mass Core layer cellulose acylate dopeabove  1 part by mass

<Manufacture of Cellulose Acylate Film 1>

The core layer cellulose acylate dope and the outer layer celluloseacylate dope were filtered through a filter paper having an average porediameter of 34 μm and a sintered metal filter having an average porediameter of 10 μm, and then all the three layers of the core layercellulose acylate dope and the outer layer cellulose acylate dopes ofboth sides were simultaneously cast on a drum at 20° C. from a castingport (band caster).

Peeling was performed in a state of a solvent content of approximately20% by mass, and the both ends of the film in the width direction werefixed with a tenter clip and dried while stretching the film at astretch ratio of 1.1 times in the transverse direction.

Thereafter, the film was transported between rolls of a heat treatmentdevice and further dried to manufacture a cellulose acylate film 1having a thickness of 40 μm.

The thickness of the core layer of the obtained cellulose acylate film 1was 36 μm and the thickness of each of the outer layers arranged on theboth sides of the core layer was 2 μm.

In addition, the in-plane retardation of the obtained cellulose acylatefilm 1 was 0 nm.

[Manufacture of Optical Film]

The composition for an optical alignment film prepared above was appliedonto one surface of the manufactured cellulose acylate film 1 with a barcoater.

After application, the film was dried for 1 minute on a hot plate at120° C. to remove the solvent, thereby forming a photoisomerizationcomposition layer having a thickness of 0.3 μm.

The obtained photoisomerization composition layer was irradiated withpolarized ultraviolet rays (10 mJ/cm², an ultra-high pressure mercurylamp used), thereby forming an optical alignment film.

Subsequently, the coating liquids 1 to 5 for forming an opticallyanisotropic film prepared above were each applied onto the opticalalignment film with a bar coater, thereby forming a composition layer.

The formed composition layer was once heated to 110° C. on a hot plateand then cooled to 60° C. to stabilize the alignment.

Thereafter, the composition layer was kept at 60° C. and irradiated withultraviolet rays (500 mJ/cm², an ultra-high pressure mercury lamp used)to fix the alignment in a nitrogen atmosphere (oxygen concentration 100ppm), thereby forming optically anisotropic films having a thickness of2.3 μm (positive A plates 1 to 5), and thus manufacturing optical films1 to 5.

The in-plane retardation of the obtained optical film was 140 nm.

[Evaluation of Light Fastness]

First, the glass substrate was set in a Xenon irradiator (SX75manufactured by Suga Test Instruments Co., Ltd.) so that the cured filmof the optically anisotropic film (positive A plate) became a surface tobe irradiated, and a sample was irradiated under a condition of 150 W/m²at a distance of 290 mm from a light source for 2 hours using a #275filter, thereby obtaining a cured film after the light fastness test,with which a residual retardation was measured.

From the initial retardation (140 nm) before the test and the residualretardation as described above, a light fastness residual rate X (%) wascalculated by the following equation.

Similarly, from the cured film of each of the polymerizable liquidcrystal compositions of Examples and Comparative Examples, a lightfastness residual rate Y (%) was calculated by the following equation.Light fastness residual rate (%)=(Residual retardation/Initialretardation)×100

From the values of the light fastness residual rate X and the lightfastness residual rate Y obtained as described above, a light fastnessimprovement rate was calculated by the following equation, and the lightfastness was evaluated in accordance with the following evaluationstandard. The results are shown in Table 2 below.Light fastness improvement rate (%)=Light fastness residual rate Y-Lightfastness residual rate X

A: The light fastness improvement rate is 10% or more.

B: The light fastness residual rate is more than 5% and less than 10%.

C: The light fastness improvement rate is more than 0% and 5% or less.

D: The light fastness improvement rate is 0% or less.

<Evaluation Results>

The results of the evaluation tests above are shown in Table 2 below.

TABLE 2 Polymerizable liquid Optically anisotropic film crystal compound(coating liquid) Positive A plate Optical film Light fastness Example 20Reverse dispersion 1 1 1 A liquid crystal 1 Example 21 Reversedispersion 2 2 2 A liquid crystal 2 Example 22 Reverse dispersion 3 3 3A liquid crystal 3 Example 23 Reverse dispersion 4 4 4 B liquid crystal4 Reverse dispersion liquid crystal 5 Forward dispersion liquid crystal2 Comparative Forward dispersion 5 5 5 C Example 23 liquid crystal 1

Example 24

[Manufacture of Positive C Plate 1]

A commercially available triacetyl cellulose film “Z-TAC” (manufacturedby Fuji Photo Film Co., Ltd.) [hereinafter simply referred to as a“cellulose acylate film 2” ] was used as a temporary support.

The cellulose acylate film 2 was passed through a dielectric heatingroll at a temperature of 60° C. to raise the film surface temperature to40° C., and then an alkaline solution having the composition shown belowwas applied onto one surface of the film at a coating amount of 14 ml/m²using a bar coater, heated to 110° C., and transported for 10 secondsunder a steam-type far-infrared heater manufactured by Noritake Co.,Ltd. Subsequently, pure water was similarly applied using a bar coaterat 3 ml/m².

Subsequently, washing with water by a fountain coater and dehydration byan air knife were repeated three times, and then the film wastransported to a drying zone at 70° C. for 10 seconds and dried, therebymanufacturing a cellulose acylate film 2 which had been subjected to analkali saponification treatment.

Alkali solution Potassium hydroxide  4.7 parts by mass Water 15.8 partsby mass Isopropanol 63.7 parts by mass Fluorine-containing surfactantSF-1  1.0 part by mass (C₁₄H₂₉O(CH₂CH₂O)₂₀H) Propylene glycol 14.8 partsby mass

A coating liquid forming an alignment film having the followingcomposition was continuously applied onto the cellulose acylate film 2which had been subjected to an alkali saponification treatment, using a#8 wire bar. The film was dried with hot air at 60° C. for 60 seconds,and further dried with a hot air at 100° C. for 120 seconds, therebyforming an alignment film.

Coating liquid for forming an alignment film Polyvinyl alcohol(manufactured by Kuraray 2.4 parts by mass Co., Ltd., PVA103) Isopropylalcohol 1.6 parts by mass Methanol  36 parts by mass Water  60 parts bymass

The following coating liquid N for forming an optically anisotropic filmwas applied onto the cellulose acylate film 2 having an alignment filmmanufactured above, aged at 60° C. for 60 seconds, and irradiated withultraviolet rays at 1,000 mJ/cm² using a 70-mW/cm² air-cooling metalhalide lamp (manufactured by Eye Graphics Co., Ltd.) in air, and thealignment state thereof was fixed to align the polymerizable liquidcrystal compound vertically, thereby manufacturing a positive C plate 1.The Rth at a wavelength of 550 nm was −60 nm.

Coating liquid N for forming an optically anisotropic film Reversedispersion liquid crystal 1 100 parts by mass Aromatic diether 1  5parts by mass Vertical aligning agent (S01) below  1 part by massVertical aligning agent (S02) below  0.5 parts by mass Ethyleneoxide-modified trimethylol propanetriacrylate  8 parts by mass (V#360,manufactured by Osaka Organic Chemical Industry Ltd.) Irgacure 907(manufactured by BASF)  3 parts by mass KAYACURE DETX (manufactured byNippon  1 part by mass Kayaku Co., Ltd.) Compound B03 below  0.4 partsby mass Methyl ethyl ketone 170 parts by mass Cyclohexanone  30 parts bymass

(In the formula of the compound B03, a=90 and b=10.)

Example 25

A positive C plate 2 was manufactured in the same manner as in Example24, except that the following coating liquid M for forming an opticallyanisotropic film was used instead of the coating liquid N for forming anoptically anisotropic film. The Rth at a wavelength of 550 nm was −60nm.

Coating liquid M for forming an optically anisotropic film Reversedispersion liquid crystal 2 100 parts by mass Aromatic diether 1  5parts by mass Vertical aligning agent (S01)  1 part by mass Verticalaligning agent (S02)  0.5 parts by mass Ethylene oxide-modifiedtrimethylol propanetriacrylate  8 parts by mass (V#360, manufactured byOsaka Organic Chemical Industry Ltd.) Irgacure 907 (manufactured byBASF)  3 parts by mass KAYACURE DETX (manufactured by Nippon  1 part bymass Kayaku Co., Ltd.) Compound B03  0.4 parts by mass Methyl ethylketone 170 parts by mass Cyclohexanone  30 parts by mass

Example 26

A positive C plate 3 was manufactured in the same manner as in Example24, except that the following coating liquid L for forming an opticallyanisotropic film was used instead of the coating liquid N for forming anoptically anisotropic film. The Rth at a wavelength of 550 nm was −60nm.

Coating liquid L for forming an optically anisotropic film Reversedispersion liquid crystal 3 100 parts by mass Aromatic diether 1  5parts by mass Vertical aligning agent (S01)  1 part by mass Verticalaligning agent (S02)  0.5 parts by mass Ethylene oxide-modifiedtrimethylol propanetriacrylate  8 parts by mass (V#360, manufactured byOsaka Organic Chemical Industry Ltd.) Irgacure 907 (manufactured byBASF)  3 parts by mass KAYACURE DETX (manufactured by Nippon  1 part bymass Kayaku Co., Ltd.) Compound B03  0.4 parts by mass Methyl ethylketone 170 parts by mass Cyclohexanone  30 parts by mass

Example 27

A positive C plate 4 was manufactured in the same manner as in Example24, except that the following coating liquid O for forming an opticallyanisotropic film was used instead of the coating liquid N for forming anoptically anisotropic film. The Rth at a wavelength of 550 nm was −60nm.

Coating liquid O for forming an optically anisotropic film Reversedispersion liquid crystal 4  80 parts by mass Reverse dispersion liquidcrystal 5  20 parts by mass Aromatic diether 1  5 parts by mass Verticalaligning agent (S01)  1 part by mass Vertical aligning agent (S02)  0.5parts by mass Ethylene oxide-modified trimethylol propanetriacrylate  8parts by mass (V#360, manufactured by Osaka Organic Chemical IndustryLtd.) Irgacure 907 (manufactured by BASF)  3 parts by mass KAYACURE DETX(manufactured by Nippon  1 part by mass Kayaku Co., Ltd.) Compound B03 0.4 parts by mass Methyl ethyl ketone 170 parts by mass Cyclohexanone 30 parts by mass

Comparative Example 24

A positive C plate 5 was manufactured in the same manner as in Example24, except that the following coating liquid P for forming an opticallyanisotropic film was used instead of the coating liquid N for forming anoptically anisotropic film. The Rth at a wavelength of 550 nm was −60nm.

Coating liquid P for forming an optically anisotropic film Forwarddispersion liquid crystal 2 100 parts by mass Aromatic diether 1  5parts by mass Vertical aligning agent (S01)  1 part by mass Verticalaligning agent (S02)  0.5 parts by mass Ethylene oxide-modifiedtrimethylol propanetriacrylate  8 parts by mass (V#360, manufactured byOsaka Organic Chemical Industry Ltd.) Irgacure 907 (manufactured byBASF)  3 parts by mass KAYACURE DETX (manufactured by  1 part by massNippon Kayaku Co., Ltd.) Compound B03  0.4 parts by mass Methyl ethylketone 170 parts by mass Cyclohexanone  30 parts by mass

[Evaluation of Light Fastness]

The glass substrate was set in a Xenon irradiator (SX75 manufactured bySuga Test Instruments Co., Ltd.) so that the cured film of the positiveC plate became a surface to be irradiated, and a sample was irradiatedunder a condition of 150 W/m² at a distance of 290 mm from a lightsource for 2 hours using a #275 filter, thereby obtaining a cured filmafter the light fastness test, with which a residual Rth was measured.

From the initial Rth (60 nm) before the test and the residual Rth, eachas described above, a light fastness residual rate X (%) was calculatedby the following equation.

Similarly, using the cured film of each of the polymerizable liquidcrystal compositions of Examples and Comparative Examples, a lightfastness residual rate Y (%) was calculated by the following equation.Light fastness residual rate (%)=(Residual Rth/Initial Rth)×100

From the values of the light fastness residual rate X and the lightfastness residual rate Y, each obtained as described above, a lightfastness improvement rate was calculated by the following equation, andthe light fastness was evaluated in accordance with the followingevaluation standard. The results are shown in Table 3 below.Light fastness improvement rate (%)=Light fastness residual rate Y-Lightfastness residual rate X

A: The light fastness improvement rate is 10% or more.

B: The light fastness residual rate is more than 5% and less than 10%.

C: The light fastness improvement rate is more than 0% and 5% or less.

D: The light fastness improvement rate is 0% or less.

<Evaluation Results>

The results of the above evaluation tests are shown in Table 3 below.

TABLE 3 Optically Polymerizable anisotropic liquid crystal film (coatingPositive Light compound liquid) C plate fastness Example 24 Reversedispersion liquid N 1 A crystal 1 Example 25 Reverse dispersion liquid M2 A crystal 2 Example 26 Reverse dispersion liquid L 3 A crystal 3Example 27 Reverse dispersion liquid O 4 B crystal 4 Reverse dispersionliquid crystal 5 Comparative Forward dispersion liquid P 5 C Example 24crystal 2

Example 28

[Manufacture of Antireflection Plate (Circularly Polarizing Plate) forOrganic EL Display Device]

<Manufacture of Circularly Polarizing Plate>

The positive C plate 1 of Example 24 was transferred to the side of theoptically anisotropic film (positive A plate 1) of the optical film 1 ofExample 20 through an adhesive, and the cellulose acylate film 2 wasremoved. Further, a polarizer was adhered to the side of the celluloseacylate film 1 of the optical film 1 through an adhesive to manufacturea circularly polarizing plate.

In addition, any of the optical film 1 (positive A plate 1) of Example20 used for the manufacture of the circularly polarizing plate, and thepositive C plate 1 of Example 24 both used the samples after theabove-mentioned evaluation of light fastness.

Example 29

A circularly polarizing plate was manufactured by the same method as inExample 28, except that the optical film 2 of Example 21 was usedinstead of the optical film 1 of Example 20, and the positive C plate 2of Example 25 was used instead of the positive C plate 1.

Example 30

A circularly polarizing plate was manufactured by the same method as inExample 28, except that the optical film 3 of Example 22 was usedinstead of the optical film 1 of Example 20, and the positive C plate 3of Example 26 was used instead of the positive C plate 1.

Example 31

A circularly polarizing plate was manufactured by the same method as inExample 28, except that the optical film 4 of Example 23 was usedinstead of the optical film 1 of Example 20, and the positive C plate 4of Example 27 was used instead of the positive C plate 1.

Comparative Example 25

A circularly polarizing plate was manufactured by the same method as inExample 28, except that the optical film 5 of Comparative Example 23 wasused instead of the optical film 1 of Example 20, and the positive Cplate 5 of Comparative Example 24 was used instead of the positive Cplate 1.

[Mounting into Organic EL Panel and Evaluation Thereof]

GALAXY SII manufactured by SAMSUNG having an organic EL panel mountedtherein was disassembled to peel the circularly polarizing plate, andadhered with an adhesive such that the side of the positive C plate ofthe circularly polarizing plate manufactured above became the panelside, thereby manufacturing a display device.

The display device was allowed to perform white display, black display,and image display, reflected light was observed upon application offluorescent light and the like at a polar angle of 60 degrees, and thedisplay qualities were evaluated in accordance with the followingstandard.

A: Light leakage in the black state is not visible at all (excellent).

B: Light leakage in the black state is very slightly visible, but isacceptable.

C: Light leakage in the black state is clearly visible.

TABLE 4 Optical film Positive C plate Display performance Example 28 1 1B Example 29 2 2 B Example 30 3 3 B Example 31 4 4 A Comparative 5 5 CExample 25

From the results shown in Table 4, it was found that in a case where theoptical ti m of the embodiment of the present invention, in particular,the optical film having two or more layers of the optically anisotropicfilms of the embodiment of the present invention, in which at least oneof the layers is a positive A plate and at least one of the other layersis a positive C plate is used in a circularly polarizing plate, thedisplay function of an organic EL display device is improved.

EXPLANATION OF REFERENCES

-   -   10 optical film    -   12 optically anisotropic film    -   14 alignment film    -   16 support    -   18 hard coat layer

What is claimed is:
 1. A polymerizable liquid crystal compositioncomprising: a polymerizable liquid crystal compound havingreverse-wavelength dispersion properties; and an aromatic polyethercompound, wherein the aromatic polyether compound includes at least onecompound selected from the group consisting of Formula (B), Formula (C)and Formula (D), and wherein the compound represented by Formula (B) isa compound represented by Formula (E) or Formula (F),

in Formula (B), R^(1B) and R^(4B) each independently represent amonovalent organic group, R^(2B), R^(3B), R^(5B), and R^(6B) eachindependently represent a hydrogen atom or a monovalent substituent, andR^(1B) and R^(2B), R^(2B) and R^(3B), R^(3B) and R^(4B), R^(4B) andR^(5B), R^(5B) and R^(6B), or R^(6B) and R^(1B) may be bonded to eachother to form a ring, in Formula (C), R^(1C), R^(2C), R^(6C), and R^(7C)each independently represent a monovalent organic group, R^(3C), R^(5C),R^(8C) and R^(11C) each independently represent a hydrogen atom or amonovalent substituent, and R^(4C), R^(9C) and R^(10C) eachindependently represent a hydrogen atom or a monovalent organic group,in Formula (D), R^(1D) represents an alkylene group having 1 to 3 carbonatoms, R^(2D), R^(3D)R^(4D), and R^(5D) each independently represent ahydrogen atom or a monovalent substituent, and R^(2D) and R^(3D), orR^(3D) and R^(4D) may be bonded to each other to form a ring,

in Formula (E), R^(1E), R^(2E), R^(3E), R^(4E), R^(5E), and R^(6E) eachindependently represent a hydrogen atom or a monovalent organic group,R^(7E), R^(9E), and R^(10E) each independently represent a hydrogen atomor a monovalent substituent, R^(8E) represents a monovalent organicgroup, and R^(1E) and R^(2E), or R^(3E) and R^(4E) may be bonded to eachother to form a ring, and in Formula (F), R^(1F) and R^(4F) eachindependently represent a monovalent organic group, and R^(2F), R^(3F),R^(5F), and R^(6F) each independently represent a hydrogen atom or amonovalent substituent.
 2. The polymerizable liquid crystal compositionaccording to claim 1, wherein the polymerizable liquid crystal compoundis a liquid crystal compound represented by Formula (I),L¹-SP¹-A¹-D³-G¹-D¹-Ar-D²-G²-D⁴-A²-SP²-L²  (I) in Formula (I), D¹, D²,D³, and D⁴ each independently represent a single bond, —CO—O—, —C(═S)O—,—CR¹R²—, —CR¹R²—CR³R⁴—, —O—CR¹R²—, —CR¹R²—O—CR³R⁴—, —CO—O—CR¹R²—,—O—CO—CR¹R²—, —CR¹R²—O—CO—CR³R⁴—, —CR¹R²—CO—O—CR³R⁴—, —NR¹—CR²R³—, or—CO—NR¹—, and R¹, R², R³, and R⁴ each independently represent a hydrogenatom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms, G¹and G² each independently represent a divalent alicyclic hydrocarbongroup having 5 to 8 carbon atoms, and one or more of —CH₂—'sconstituting the alicyclic hydrocarbon group may be substituted with—O—, —S—, or —NH—, A¹ and A² each independently represent an aromaticring having 6 or more carbon atoms or a cycloalkylene ring having 6 ormore carbon atoms, SP¹ and SP² each independently represent a singlebond, a linear alkylene group having 1 to 12 carbon atoms, a branchedalkylene group having 3 to 12 carbon atoms, or a divalent linking groupin which one or more of —CH₂—'s constituting the linear alkylene grouphaving 1 to 12 carbon atoms or the branched alkylene group having 3 to12 carbon atoms are substituted with —O—, —S—, —NH—, —N(Q)-, or —CO—,and Q represents a substituent, L¹ and L² each independently represent amonovalent organic group, and at least one of L¹ or L² represents apolymerizable group, provided that in a case where Ar is an aromaticring represented by Formula (Ar-3), at least one of L¹, L², or L³ or L⁴in Formula (Ar-3) represents a polymerizable group, Ar represents anyone aromatic ring selected from the group consisting of groupsrepresented by Formulae (Ar-1) to (Ar-5),

here, in Formulae (Ar-1) to (Ar-5), *1 represents a bonding positionwith D¹ and *2 represents a bonding position with D², Q¹ represents N orCH, Q² represents —S—, —O—, or —N(R⁵)—, and R⁵ represents a hydrogenatom or an alkyl group having 1 to 6 carbon atoms, Y¹ represents anaromatic hydrocarbon group having 6 to 12 carbon atoms or aromaticheterocyclic group having 3 to 12 carbon atoms, which may have asubstituent, Z¹, Z², and Z³ each independently represent a hydrogenatom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbonatoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbonatoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbonatoms, a halogen atom, a cyano group, a nitro group, —NR⁶R⁷, or —SR⁸, R⁶to R⁸ each independently represent a hydrogen atom or an alkyl grouphaving 1 to 6 carbon atoms, and Z¹ and Z² may be bonded to each other toform an aromatic ring, A³ and A⁴ each independently represent a groupselected from the group consisting of —O—, —N(R⁹)—, —S—, and —CO—, andR⁹ represents a hydrogen atom or a substituent, X represents a hydrogenatom or a non-metal atom of Groups 14 to 16 to which a substituent maybe bonded, D⁵ and D⁶ each independently represent a single bond, —CO—O—,—C(═S)O—, —CR¹R²—, —CR¹R²—CR³R⁴—, —O—CR¹R²—, —CR¹R²—O—CR³R⁴—,—CO—O—CR¹R²—, —O—CO—CR¹R²—, —CR¹R²—O—CO—CR³R⁴—, —CR¹R²—CO—O—CR³R⁴—,—NR¹—CR²R³—, or —CO—NR¹—, and R¹, R², R³, and R⁴ each independentlyrepresent a hydrogen atom, a fluorine atom, or an alkyl group having 1to 4 carbon atoms, SP³ and SP⁴ each independently represent a singlebond, a linear alkylene group having 1 to 12 carbon atoms, a branchedalkylene group having 3 to 12 carbon atoms, or a divalent linking groupin which one or more of —CH₂—'s constituting the linear alkylene grouphaving 1 to 12 carbon atoms or the branched alkylene group having 3 to12 carbon atoms are substituted with —O—, —S—, —NH—, —N(Q)-, or —CO—,and Q represents a substituent, L³ and L⁴ each independently represent amonovalent organic group, and at least one of L³, L⁴, or L¹ or L² inFormula (I) represents a polymerizable group, Ax represents an organicgroup having 2 to 30 carbon atoms, which has at least one aromatic ringselected from the group consisting of an aromatic hydrocarbon ring andan aromatic heterocyclic ring, Ay represents a hydrogen atom, an alkylgroup having 1 to 6 carbon atoms which may have a substituent, or anorganic group having 2 to 30 carbon atoms, which has at least onearomatic ring selected from the group consisting of an aromatichydrocarbon ring and an aromatic heterocyclic ring, the aromatic ringsin Ax and Ay may have a substituent, and Ax and Ay may be bonded to eachother to form a ring, and Q³ represents a hydrogen atom or an alkylgroup having 1 to 6 carbon atoms which may have a substituent.
 3. Thepolymerizable liquid crystal composition according to claim 2, wherein acompound used for forming the aromatic rings represented by Formulae(Ar-1) to (Ar-5) represented by Ar in Formula (I) is a compound thatcontains a phenolic structure in which *1 and *2 in Formulae (Ar-1) to(Ar-5) represent hydroxyl groups, and a pKa of the is 5.8 to 10.0. 4.The polymerizable liquid crystal composition according to claim 1,wherein a content of the aromatic polyether compound is 0.1 to 50 partsby mass with respect to 100 parts by mass of the polymerizable liquidcrystal compound.
 5. An optically anisotropic film comprising thepolymerizable liquid crystal composition according to claim
 1. 6. Anoptical film comprising the optically anisotropic film according toclaim
 5. 7. The optical film according to claim 6, wherein the opticallyanisotropic film is a positive A plate or a positive C plate.
 8. Theoptical film according to claim 6, comprising two or more layers of theoptically anisotropic films, wherein at least one of the layers is apositive A plate and at least one of the other layers is a positive Cplate.
 9. A polarizing plate comprising: the optical film according toclaim 6; and a polarizer.
 10. An image display device comprising theoptical film according to claim
 6. 11. An organic electroluminescentdisplay device comprising: an organic electroluminescent display panel;and a circularly polarizing plate arranged on the organicelectroluminescent display panel, wherein the circularly polarizingplate includes a polarizer and the optical film according to claim 8.